Azzindani/Open_Reaction_Data huggingface dataset:
Reaction SMILES: [CH3:1][N:2]([CH3:39])[CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:38])/[C:14](/[C:28]2[CH:33]=[CH:32][C:31]([O:34]COC)=[CH:30][CH:29]=2)=[C:15](/[C:18]2[CH:23]=[CH:22][C:21]([O:24]COC)=[CH:20][CH:19]=2)\[CH2:16][CH3:17])=[CH:8][CH:7]=1.Cl.C([O-])(O)=O.[Na+]>CO.CCOC(C)=O.O>[CH3:39][N:2]([CH3:1])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([NH:12][C:13](=[O:38])/[C:14](/[C:28]2[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=2)=[C:15](/[C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=2)\[CH2:16][CH3:17])=[CH:10][CH:11]=1
Reactant: CC/C(=C(\C(=O)Nc1ccc(OCCN(C)C)cc1)c1ccc(OCOC)cc1)c1ccc(OCOC)cc1
Agent: Cl
Agent: O=C([O-])O
Agent: [Na+]
Solvent: CCOC(C)=O
Solvent: O
Solvent: CO
Product: CC/C(=C(\C(=O)Nc1ccc(OCCN(C)C)cc1)c1ccc(O)cc1)c1ccc(O)cc1
Temperature: 25 °C
Reaction time: 2 h
Yield: 68 %

Procedure:
To a solution of 4a (45 mg, 0.0842 mmol) in MeOH (1 ml) was added 3N HCl in AcOEt (0.5 ml) under ice cooling, and the mixture was stirred at room temperature for 2 h. A solution of NaHCO3 (126 mg) in H2O was poured into the reaction mixture under ice cooling, and the whole was extracted with AcOEt and a little MeOH. The organic layer was washed with brine, dried over Na2SO4, and then concentrated. The residual solid was crystallized with Et2O to give 5 (68%). 5: colorless powder; 1H-NMR (CD3OD) δ 0.98 (3H, t, J=7.4 Hz), 2.45 (6H, s), 2.61 (2H, q, J=7.4 Hz), 2.90 (2H, t, J=5.3 Hz), 4.14 (2H, t, J=5.3 Hz), 6.54 (2H, d, J=8.8 Hz), 6.63 (2H, d, J=8.6 Hz), 6.92-6.97 (6H, m), 7.52 (2H, d, J=9.0 Hz). HRMS calcd for C27H31N2O4 [M+H]+: 447.2284. Found: 447.2298.
Reaction SMILES: COC1C=CC(N2CCN(C3C=CC([N:21]4[CH:25]=[N:24][NH:23][C:22]4=[O:26])=CC=3)CC2)=CC=1.[H-].[Na+].Br[CH2:30][CH2:31][CH3:32]>CS(C)=O>[CH2:30]([N:23]1[C:22](=[O:26])[N:21]=[CH:25][NH:24]1)[CH2:31][CH3:32]
Reactant: CCCBr
Reactant: COc1ccc(N2CCN(c3ccc(-n4cn[nH]c4=O)cc3)CC2)cc1
Agent: [H-]
Agent: [Na+]
Solvent: CS(C)=O
Product: CCCn1[nH]cnc1=O
Temperature: 50 °C

Procedure:
10 Parts of 2,4-dihydro-4-{4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl}-3H-1,2,4-triazol-3-one are dissolved in 300 parts of dimethyl sulfoxide at 100° C. Then there are added 1.6 parts of sodium hydride dispersion 50% and stirring is continued while the mixture is allowed to cool to about 50° C. 3.9 Parts of 1-bromopropane are added and the whole is stirred overnight at room temperature. The reaction mixture is poured onto water and the product is extracted with trichloromethane. The extract is washed with water, dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (98:2 by volume) as eluent. The pure fractions are collected and the eluent is evaporated. The residue is triturated in 2-propanol. The product is filtered off and dried; yielding 7.5 parts (65%) of 2,4-dihydro-4-55 4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl}-2-propyl-3H-1,2,4 -triazol-3-one.
Reaction SMILES: [CH3:1][O:2][C:3]1[CH:4]=[C:5](/[CH:13]=[CH:14]/[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[CH2:9][CH3:10].[CH3:21][O:22][C:23]1[CH:24]=[C:25](/[CH:32]=[CH:33]/[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:26]=[C:27]([O:30][CH3:31])[C:28]=1Br.C(I)C>C1COCC1.O>[CH3:12][O:11][C:7]1[CH:6]=[C:5](/[CH:13]=[CH:14]/[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:4]=[C:3]([O:2][CH3:1])[C:8]=1[CH2:9][CH3:10].[CH3:31][O:30][C:27]1[CH:26]=[C:25](/[CH:32]=[CH:33]/[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:24]=[C:23]([O:22][CH3:21])[CH:28]=1
Reactant: COc1cc(/C=C/c2ccccc2)cc(OC)c1Br
Agent: CCc1c(OC)cc(/C=C/c2ccccc2)cc1OC
Solvent: CCI
Solvent: O
Solvent: C1CCOC1
Product: COc1cc(/C=C/c2ccccc2)cc(OC)c1
Temperature: -78 °C
Yield: 30 %

Procedure:
3,5-Dimethoxy-4-ethyl-trans-stilbene (compound 15A-a in Scheme 5): t-butyl Li (1.1 mL, 1M in THF) was added at −78° C. to a THF solution (10 mL) containing 3,5-dimethoxy-4-bromo-trans-stilbene (0.53 g). After addition, the solution was slowly heated to reflux for 30 min and then cooled down to −78° C. Ethyl iodide (1.2 eq, 0.265 mL) was added to the solution at −78° C. After reaction finished, water (10 mL) was added dropwise to the mixture, THF was evaporated under reduced pressure. The mixture was extracted with CH2Cl2 (5 mL×3), the combined organic layer was dried over anhydrous magnesium sulfate, and remove under reduced pressure. The product mixture was purified by column chromatography (ether/pet ether=1:8) and gave 3,5-dimethoxy-4-ethyl-trans-stilbene (15A-a) (70%) and 3,5-dimethoxy-trans-stilbene (30%) due to the moisture. Mp: 70-73° C. NMR (400 MHz, CDCl3): δ 1.12 (t, 6H, J=7.2 Hz, CH3), 2.70 (q, 2H, —CH2—), 3.91 (s, 6H, OCH3), 6.74 (s, 2H, H-2, 6), 7.07 (s, 2H), 7.26 (m, 1H, H-4′), 7.36 (m, 2H, H-3′, 5′), 7.52 (m, 2H, H-2′, 6′).
Reaction SMILES: [C:1]1([C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][CH2:17][C:18]#[N:19])[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[NH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][N:11]1[CH2:12][CH2:13][C:8](=[C:7]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:9][CH2:10]1
Reactant: N#CCCCCN1CCC(=C(c2ccccc2)c2ccccc2)CC1
Agent: [Al+3]
Agent: [H-]
Agent: [Li+]
Product: NCCCCCN1CCC(=C(c2ccccc2)c2ccccc2)CC1
Yield: 36 %

Procedure:
The title compound was prepared in a yield of 36% in a similar manner to that described in Preparation 41' by reacting 4-(diphenylmethylene)-1-(4-cyanobutyl)-piperidine (prepared as described in Preparation 39') and lithium aluminum hydride.
Reaction SMILES: [CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:7](=[O:22])[N:8]3[CH2:21][CH2:20][CH2:19][CH:9]3[N:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:11]=2[CH:12]=1.Br[CH2:24][CH2:25]CCCC(Cl)=O.BrCCCCC1NC(=O)C2C(=CC(OC)=CC=2)N1C1C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7](=[O:22])[N:8]3[CH2:21][CH2:25][CH2:24][CH2:20][CH2:19][CH:9]3[N:10]2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:5][CH:4]=1
Reactant: O=C(Cl)CCCCCBr
Reactant: COc1ccc2c(c1)N(c1ccccc1)C1CCCN1C2=O
Agent: COc1ccc2c(c1)N(c1ccccc1)C(CCCCBr)NC2=O
Agent: O=C([O-])[O-]
Agent: [Cs+]
Solvent: CN(C)C=O
Product: COc1ccc2c(c1)N(c1ccccc1)C1CCCCCN1C2=O
Temperature: 25 °C
Reaction time: 72 h

Procedure:
Following the procedure for 6-methoxy-4-phenyl-2,3,3a,4-tetrahydropyrrolo[2,1-b]quinazolin-9(1H)-one, using 6-bromohexanoyl chloride in place of 4-bromobutyryl chloride, 410 mg of an intermediate presumed to be 2-(4-bromobutyl)-7-methoxy-1-phenyl-2,3-dihydroquinazolin-4(1H)-one. 200 mg of this material was dissolved in 2 mL DMF and treated with cesium carbonate (450 mg). The reaction was stirred at room temp for 72 h, then partitioned between EtOAc and water. The organic solution was dried (Na2SO4) and concentrated. Flash chromatography (50% EtOAc in hexanes) gave the titled compound.
Reaction SMILES: [CH3:1][C:2]1[CH:3]=[C:4]([S:9]([CH2:11][C:12]#[CH:13])=O)[CH:5]=[C:6]([CH3:8])[CH:7]=1.[BrH:14].C(OCC)(=O)C>C(OCCC)(=O)C>[Br:14][CH2:13][C:12]1[C:3]2[C:2]([CH3:1])=[CH:7][C:6]([CH3:8])=[CH:5][C:4]=2[S:9][CH:11]=1
Reactant: C#CCS(=O)c1cc(C)cc(C)c1
Reactant: Br
Solvent: CCCOC(C)=O
Solvent: CCOC(C)=O
Product: Cc1cc(C)c2c(CBr)csc2c1
Reaction time: 0.5 h
Yield: 84 %

Procedure:
In 40 mL of propyl acetate, was dissolved 2.26 g (11.7 mmol) of the compound obtained in Example 13. The refluxing was carried out for 30 minutes. The solution was then cooled, and 1.59 mL (14 mmol) of a 48% hydrobromic acid was added. The resulting mixture was allowed to stand at room temperature for 30 minutes. Ethyl acetate was subsequently added, and the obtained mixture was washed with water, dried with magnesium sulfate and vacuum concentrated to obtain 2.49 g of 3-(bromomethyl)-4,6-dimethylbenzo[b]thiophene. The yield was 84%.
Reaction SMILES: [CH2:1]([O:3][P:4]([CH:9]([OH:13])[C:10]([OH:12])=[O:11])([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].[C:14]1(C)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CO>[O:11]=[C:10]1[O:12][C:14]2([CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[O:13][CH:9]1[P:4](=[O:5])([O:3][CH2:1][CH3:2])[O:6][CH2:7][CH3:8]
Reactant: CCOP(=O)(OCC)C(O)C(=O)O
Reactant: Cc1ccccc1
Solvent: CO
Product: CCOP(=O)(OCC)C1OC2(CCCCC2)OC1=O
Temperature: 110 °C

Procedure:
In a reaction vessel with a descending condenser, 50 g (0.236 Mol) (diethoxyphosphinyl)-hydroxyacetic acid (A) and 240 mL toluene are mixed at ambient temperature and then heated to 110° C. When the boiling temperature of toluene is reached, a mixture of 71.7 mL (0.471 Mol) cyclohexane-dimethylketal (B) and 10 mL toluene are slowly added dropwise, while the azeotrope of toluene and methanol is distilled off. After the addition has ended the reaction mixture is refluxed for 90 minutes. Any solvent distilled off is replaced by the addition of 50 mL toluene. In order to achieve total conversion, a further 10 mL (0.066 Mol) of cyclohexane-dimethylketal (B) are added dropwise. The mixture is heated to a 110° C. for another hour and the solvent distilled off is replaced by the addition of another 100 mL toluene. After the addition of another 120 mL toluene the solvent is distilled off in vacuo. The residue is taken up in 200 mL tert.butyl-methylether and successively extracted twice with 200 mL of 10% potassium carbonate solution, once with 250 mL of 30% sodium bisulphite solution and once with 150 mL of 30% sodium bisulphite solution. After subsequent extraction with 40 mL saturated saline solution the organic phase is dried and evaporated down.
Reaction SMILES: [BH4-].[Na+].C1COCC1.C[O:9][C:10](=O)[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][N:18]([CH2:27][CH2:28][CH2:29][O:30][C:31]2[CH:32]=[C:33]3[C:38](=[CH:39][CH:40]=2)[N:37]([CH3:41])[C:36](=[O:42])[CH:35]=[CH:34]3)[CH2:19][CH2:20][C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)[CH:12]=1.[ClH:44]>C(OCC)(=O)C.O.CO>[ClH:44].[ClH:44].[OH:9][CH2:10][C:11]1[CH:12]=[C:13]([CH:14]=[CH:15][CH:16]=1)[CH2:17][N:18]([CH2:27][CH2:28][CH2:29][O:30][C:31]1[CH:32]=[C:33]2[C:38](=[CH:39][CH:40]=1)[N:37]([CH3:41])[C:36](=[O:42])[CH:35]=[CH:34]2)[CH2:19][CH2:20][C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1
Reactant: COC(=O)c1cccc(CN(CCCOc2ccc3c(ccc(=O)n3C)c2)CCc2cccnc2)c1
Agent: Cl
Agent: [BH4-]
Agent: [Na+]
Solvent: O
Solvent: CO
Solvent: CCOC(C)=O
Product: Cn1c(=O)ccc2cc(OCCCN(CCc3cccnc3)Cc3cccc(CO)c3)ccc21
Temperature: 25 °C
Reaction time: 1.5 h

Procedure:
Sodium borohydride (16.5 mg) was added to a THF solution (4 ml) of 3-{[N-[3-(1-methyl-2-oxo-1,2-dihydroquinolin-6-yloxy)propyl]-N-(2-pyridin-3-ylethyl)amino]methyl}benzoic acid methyl ester (192 mg). Methanol (1 ml) was added to the mixture and stirred for 1.5 hour while heated under reflux. The reaction liquid was cooled to room temperature. Water was added to the reaction mixture, followed by extraction with dichloromethane. The organic layer was dried over anhydrous sodium sulfate. The filtrate was condensed under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate: methanol=10:1→4:1). The purified product was condensed under reduced pressure. A 4N-hydrogen chloride in ethyl acetate solution(0.082 ml) was added to a ethyl acetate solution (1 ml) of the residue, and the liquid was stirred at room temperature. The precipitated insoluble matter was separated, washed with ether, and dried to give the title compound(53.4 mg) as a white powder.
Reaction SMILES: Br[C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:11]2[CH2:16][CH2:15][C@:14]([CH2:23][CH3:24])([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[O:13][C:12]2=[O:25])[CH2:9][CH3:10])=[CH:4][CH:3]=1.Br[C:27]1[CH:28]=[CH:29][C:30](=[O:36])[N:31]([CH:33]([CH3:35])[CH3:34])[CH:32]=1>>[CH2:23]([C@@:14]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[O:13][C:12](=[O:25])[N:11]([C@H:8]([C:5]2[CH:6]=[CH:7][C:2]([C:27]3[CH:28]=[CH:29][C:30](=[O:36])[N:31]([CH:33]([CH3:35])[CH3:34])[CH:32]=3)=[CH:3][CH:4]=2)[CH2:9][CH3:10])[CH2:16][CH2:15]1)[CH3:24]
Reactant: CC[C@@H](c1ccc(Br)cc1)N1CC[C@](CC)(c2ccccc2)OC1=O
Reactant: CC(C)n1cc(Br)ccc1=O
Product: CC[C@@H](c1ccc(-c2ccc(=O)n(C(C)C)c2)cc1)N1CC[C@](CC)(c2ccccc2)OC1=O

Procedure:
The title compound was prepared from (R)-3-((S)-1-(4-bromophenyl)propyl)-6-ethyl-6-phenyl-1,3-oxazinan-2-one following procedures analogous to those described in Example 32 Method 2 Steps 3 and 4 using 5-bromo-1-isopropylpyridin-2(1H)-one in Step 4. LC-MS Method 1 tR=1.75 min, m/z=459 (M+1); 1H NMR (CDCl3) 7.49, (1H, dd, J=2.34, 9.37 Hz), 7.42 (1H, d, J=2.34 Hz), 7.32-7.24 (5H, m), 7.13 (1H, d, J=8.20), 7.04 (1H, d, J=8.49), 6.66 (1H, d, J=9.37), 5.49 (1H, aq q, J=6.44, 9.37), 5.33 (1H, m), 2.96-2.91 (1H, m), 2.39-2.32 (1H, m), 2.29-2.17 (2H, m), 2.05-1.85 (m, 4H), 1.41 (6H, dd, J=1.17, 6.73), 1.01 (3H, t, J=7.32 Hz), 0.832 (3H, t, J=7.32 Hz).
Reaction SMILES: Cl[C:2]1[C:3]([C:20]([NH2:22])=[O:21])=[N:4][C:5]([CH2:18][CH3:19])=[C:6]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=2)[N:7]=1.[CH3:23][N:24]1[CH2:29][CH2:28][N:27]([CH:30]2[CH2:35][CH2:34][N:33]([C:36]3[CH:42]=[CH:41][C:39]([NH2:40])=[CH:38][CH:37]=3)[CH2:32][CH2:31]2)[CH2:26][CH2:25]1.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>CN1CCCC1=O>[CH2:18]([C:5]1[N:4]=[C:3]([C:20]([NH2:22])=[O:21])[C:2]([NH:40][C:39]2[CH:41]=[CH:42][C:36]([N:33]3[CH2:34][CH2:35][CH:30]([N:27]4[CH2:28][CH2:29][N:24]([CH3:23])[CH2:25][CH2:26]4)[CH2:31][CH2:32]3)=[CH:37][CH:38]=2)=[N:7][C:6]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=1)[CH3:19]
Reactant: CCc1nc(C(N)=O)c(Cl)nc1Oc1cccc([N+](=O)[O-])c1
Reactant: CN1CCN(C2CCN(c3ccc(N)cc3)CC2)CC1
Agent: O=C([O-])O
Agent: [Na+]
Solvent: O=C(O)C(F)(F)F
Solvent: CN1CCCC1=O
Product: CCc1nc(C(N)=O)c(Nc2ccc(N3CCC(N4CCN(C)CC4)CC3)cc2)nc1Oc1cccc([N+](=O)[O-])c1
Temperature: 150 °C
Yield: 55.1 %

Procedure:
A mixture of 3-chloro-6-ethyl-5-(3-nitrophenoxy)pyrazine-2-carboxamide (400 mg), 4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]aniline (374 mg), trifluoroacetic acid (209 μL), and N-methylpyrrolidone (2.8 mL) was heated at 150° C. for 16 hours. To the reaction mixture was added a saturated aqueous sodium hydrogen carbonate solution, and the precipitated solid was collected by filtration, and then dried. The obtained solid was purified by silica gel column chromatography (eluent; chloroform:methanol:28% aqueous ammonia=1:0:0-200:10:1) to obtain 6-ethyl-3-({4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}amino)-5-(3-nitrophenoxy)pyrazine-2-carboxamide (383 mg) as a brown solid.
Reaction SMILES: Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=1[Cl:25])[N:6]2[C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1.[N:26]12CCN(CC1)C[CH2:27]2>C(#N)C.[C-]#N.C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:17][C:14]1[CH:13]=[CH:12][C:11]([N:6]2[C:5]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=3[Cl:25])=[N:4][C:3]3[C:7]2=[N:8][CH:9]=[N:10][C:2]=3[C:27]#[N:26])=[CH:16][CH:15]=1
Reactant: Clc1ccc(-n2c(-c3ccc(Cl)cc3Cl)nc3c(Cl)ncnc32)cc1
Reactant: C1CN2CCN1CC2
Agent: CCCC[N+](CCCC)(CCCC)CCCC
Agent: [C-]#N
Solvent: CC#N
Product: N#Cc1ncnc2c1nc(-c1ccc(Cl)cc1Cl)n2-c1ccc(Cl)cc1
Temperature: 0 °C
Reaction time: 3 h

Procedure:
6-Chloro-9-(4-chlorophenyl)-8-(2,4-dichlorophenyl)-9H-purine I-(1A-1)d (200 mg, 0.49 mmol) was dissolved in acetonitrile (5 ml) and stirred at 0° C. Tetrabutylammonium cyanide (236 mg, 0.98 mmol) and 1,4-diaza-bicyclo[2.2.2]octane (173 mg, 1.5 mmol) were added to the reaction mixture and stirring was continued at 0° C. for 3 hours. The reaction mixture was concentrated under reduced pressure and then purified by flash chromatography using 30% ethyl acetate/hexanes as the eluant to obtain the desired product I-(16A-1)a (215 mg, quant): +ESI MS (M+1) 400.2; 1H NMR (400 MHz, CDCl3) δ 9.09 (s, 1H), 7.57 (d, J=8.7 Hz, 1H), 7.45–7.39 (m, 4H), 7.21 (d, J=8.7 Hz, 2H).
Reaction SMILES: [Na].[CH2:2]([N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][NH:18][S:19]([CH2:22][CH2:23][CH2:24]Cl)(=[O:21])=[O:20])[CH2:11][CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>C(O)C>[CH2:2]([N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][N:18]2[CH2:24][CH2:23][CH2:22][S:19]2(=[O:21])=[O:20])[CH2:11][CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1
Reactant: O=S(=O)(CCCCl)NCCCN1CCN(Cc2ccccc2)CC1
Agent: [Na]
Solvent: CCO
Product: O=S1(=O)CCCN1CCCN1CCN(Cc2ccccc2)CC1
Reaction time: 24 h

Procedure:
Sodium (0.23 g/10.0 mmol) was added to ethanol (20 ml). To the resulting solution was added N-[3-(4-benzyl-1-piperazinyl)propyl]-3-chloro-1-propanesulfonamide in ethanol (20 ml) and the mixture was stirred for 1 day at reflux temperature. The solvent was removed in vacuo and the residue was diluted with dichloromethane (50 ml) and water (50 ml). The aqueous layer was extracted with dichloromethane (50 ml). The combined extracts were washed with brine (50 ml), dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (NH2 gel/dichloromethane) to give a colorless oil (0.60 g/21%).