Azzindani/Open_Reaction_Data huggingface dataset:
Reaction SMILES: BrC1C=CC([O:6]CC(O)C)=CC=1.CS(C)=O.[CH:17]1([N:23]=[C:24]=[N:25][CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.FC(F)(F)C(O)=O.C(O)(=O)C(O)=O>CCOCC.CO.N1C=CC=CC=1>[CH:26]1([NH:25][C:24](=[O:6])[NH:23][CH:17]2[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]2)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1
Reactant: CC(O)COc1ccc(Br)cc1
Reactant: C(=NC1CCCCC1)=NC1CCCCC1
Agent: O=C(O)C(=O)O
Solvent: CCOCC
Solvent: CO
Solvent: c1ccncc1
Product: O=C(NC1CCCCC1)NC1CCCCC1

Procedure:
A solution is prepared from 43.35 g (0.1 mol) 3-[2-(2-propinoxycarbonyl)-ethyl]-phenoxy)-1-(4'-bromophenoxy)-propane-2-ol in 500 ml absolute ether and mixed at room temperature with 40 mol dimethylsulfoxide, 7 ml pyridine and 30.95 g (0.15 mol) dicyclohexylcarbodiimide. After adding 5 ml trifluoroacetic acid, the mixture is stirred until no starting compound can be determined through thin-layer chromatographic control. In order to eliminate excessive dicyclohexylcarbodiimide, the reaction mixture is mixed in portions with a solution of 30 g oxalic acid in methanol and stirred for 20 minutes. After the dicyclohexyl-urea precipitate formed is separated, the filtrate is washed with a solution of sodium hydrocarbonate and then with water. The organic phase is dried over sodium sulfate and concentrated in vacuo. The raw product is recrystallized twice. Colorless crystals, melting point 90°-1° C. (isopropanol): yield 37.56 g (87.1%).
Reaction SMILES: ClC[CH2:3][CH2:4][N:5]([CH3:7])[CH3:6].[CH2:8]([O:10][C:11](=[O:23])[C:12]([C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16][CH:15]=1)=[O:13])[CH3:9].C([O-])([O-])=O.[Cs+].[Cs+]>>[CH2:8]([O:10][C:11](=[O:23])[C:12]([C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]([CH2:3][CH2:4][N:5]([CH3:7])[CH3:6])[CH:15]=1)=[O:13])[CH3:9]
Reactant: CCOC(=O)C(=O)c1c[nH]c2ccccc12
Reactant: CN(C)CCCCl
Agent: O=C([O-])[O-]
Agent: [Cs+]
Product: CCOC(=O)C(=O)c1cn(CCN(C)C)c2ccccc12
Yield: 63.3 %

Procedure:
The general procedure 1 was then followed using 1-chloro-3-dimethylaminopropane (7 mmol, 0.75 g), ethyl-2-(1H-indol-3-yl)-2-oxoacetate (6 mmol, 1.3 g) and Cs2CO3 (6.6 mmol, 2.15 g). The purification was achieved by column chromatography (petrolether:ethylacetate:diethylamine 6:3:1) to yield ethyl-2-{1-[2-(dimethylamino)ethyl]-1H-indol-3-yl}-2-oxoacetate (3.8 mmol, 63%) as an pale yellow oil. IR {tilde over (ν)} [cm−1]=3023; 2962; 2917; 1732; 1630. EI-MS m/z (rel. int.)=302 (8.21%; M+•). 1H NMR (300 MHz, CDCl3) 8.43 (m; 1H; indole-H); 8.39 (s; 1H; indole-H); 7.33 (m; 3H; indole-H); 4.40 (q; 3J=7.1 Hz; 2H; OCH2CH3); 4.27 (t; 3J=6.8 Hz; 2H; indole-CH2CH2CH2N); 2.22 (s; 6H; N(CH3)2); 2.20 (m; 2H; indole-CH2CH2CH2N); 2.00 (quint; 3J=6.7 Hz; 2H; indole-CH2CH2CH2N); 1.42 (t; 3J=7.1 Hz; 3HOCH2CH3).
Reaction SMILES: [Cl:1][C:2]1[C:11]([C:12]([NH:14][NH2:15])=[O:13])=[C:10]([S:16]([CH3:19])(=[O:18])=[O:17])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH:20](OCC)(OCC)OCC>>[Cl:1][C:2]1[C:11]([C:12]2[O:13][CH:20]=[N:15][N:14]=2)=[C:10]([S:16]([CH3:19])(=[O:18])=[O:17])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]
Reactant: COC(=O)c1ccc(S(C)(=O)=O)c(C(=O)NN)c1Cl
Reactant: CCOC(OCC)OCC
Product: COC(=O)c1ccc(S(C)(=O)=O)c(-c2nnco2)c1Cl

Procedure:
1.16 g (3.8 mmol) of methyl 2-chloro-3-hydrazinocarbonyl-4-methylsulfonylbenzoate and 10 ml of triethyl orthoformate were heated under reflux for 6 hours. The precipitate that had formed was filtered off with suction, washed with n-hexane and subsequently taken up in 20 ml of toluene. After the addition of p-toluenesulfonic acid, the mixture was heated at reflux for 3 hours and then cooled, washed with water, dried and concentrated. 0.62 g (52% of thoery) of methyl 2-chloro-4-methylsulfonyl-3-(1,3,4-oxadiazol-2-yl)benzoate was obtained.
Reaction SMILES: [Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[OH:9].C([O-])([O-])=O.[K+].[K+].[CH3:16][C:17]([CH3:19])=O>>[CH2:16]([O:9][C:3]1[C:4]([F:8])=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1])[C:17]1[CH:19]=[CH:4][CH:3]=[CH:2][CH:7]=1
Reactant: CC(C)=O
Reactant: Oc1c(F)cccc1Cl
Agent: O=C([O-])[O-]
Agent: [K+]
Product: Fc1cccc(Cl)c1OCc1ccccc1
Temperature: 65 °C

Procedure:
A mixture of 2-chloro-6-fluorophenol (25 g, 170 mmol), acetone (200 ml), K2CO3 (47.08 g, 340 mmol) and bensylbromide (22.31 ml, 187 mmol) was heated at 65° C. for 16 h. The solution was filtered and evaporated. Water (100 ml) was added, and the solution was extracted with EtOAc. The combined organic phases were dried (Na2SO4) and evaporated to dryness to give the title compound (32.3 g). MS m/z (rel. intensity, 70 eV) 236 (M+, 2), 117 (4), 92 (8), 91 (bp), 65 (13).
Reaction SMILES: [CH3:1][S:2](Cl)(=[O:4])=[O:3].[C:6]1(/[CH:12]=[CH:13]/[C:14]2[O:15][CH:16]=[C:17]([CH2:19][S:20][C:21]3[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][CH2:29][OH:30])=[CH:23][CH:22]=3)[N:18]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(N(CC)CC)C.O>O1CCCC1>[CH3:1][S:2]([O:30][CH2:29][CH2:28][CH2:27][C:24]1[CH:23]=[CH:22][C:21]([S:20][CH2:19][C:17]2[N:18]=[C:14](/[CH:13]=[CH:12]/[C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=3)[O:15][CH:16]=2)=[CH:26][CH:25]=1)(=[O:4])=[O:3]
Reactant: OCCCc1ccc(SCc2coc(/C=C/c3ccccc3)n2)cc1
Reactant: CS(=O)(=O)Cl
Solvent: CCN(CC)CC
Solvent: C1CCOC1
Solvent: O
Product: CS(=O)(=O)OCCCc1ccc(SCc2coc(/C=C/c3ccccc3)n2)cc1
Temperature: 25 °C
Reaction time: 4 h
Yield: 88.4 %

Procedure:
Methanesulfonyl chloride (320 mg) was added to a solution of 3-[4-[2-[(E)-2-phenylethenyl]-4-oxazolylmethylthio]phenyl]propanol (500 mg) and triethylamine (280 mg) in tetrahydrofuran (30 ml) at 0° C. and then stirred for 4 hours at room temperature. To the reaction mixture was added water, and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4), and concentrated under reduced pressure to give 3-[4-[2-[(E)-2-phenylethenyl]-4-oxazolylmethylthio]phenyl]propyl methanesulfonate (540 mg, 90%). Recrystallization from ethyl acetate-hexane gave pale yellow prisms, mp 97-98° C.
Reaction SMILES: Cl.Cl[CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1.[N+:11]([C:14]1[CH:15]=[C:16]([OH:20])[CH:17]=[CH:18][CH:19]=1)([O-])=O>>[NH2:11][C:14]1[CH:15]=[C:16]([CH:17]=[CH:18][CH:19]=1)[O:20][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1
Reactant: O=[N+]([O-])c1cccc(O)c1
Reactant: ClCCN1CCOCC1
Agent: Cl
Product: Nc1cccc(OCCN2CCOCC2)c1

Procedure:
By the method of examples 2 and 3, 4-(2-chloroethyl)morpholine hydrochloride and 3-nitrophenol were converted into the title compound.
Reaction SMILES: [CH3:1][Mg]Br.CON(C)[C:7](=[O:19])[C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH:18]=[CH:17][CH:16]=[N:15]2)=[N:10][CH:9]=1>O1CCCC1>[N:14]1([C:11]2[N:10]=[CH:9][C:8]([C:7](=[O:19])[CH3:1])=[CH:13][CH:12]=2)[CH:18]=[CH:17][CH:16]=[N:15]1
Reactant: C[Mg]Br
Reactant: CON(C)C(=O)c1ccc(-n2cccn2)nc1
Solvent: C1CCOC1
Product: CC(=O)c1ccc(-n2cccn2)nc1
Temperature: 25 °C
Reaction time: 8 h

Procedure:
Methylmagnesium bromide (3 M in tetrahydrofuran) (3.16 mL, 9.5 mmol) was added to a −78° C. solution of N-methoxy-N-methyl-6-(1H-pyrazol-1-yl)nicotinamide (2.0 g, 8.6 mmol) in tetrahydrofuran (10 mL). After stirring at ambient temperature overnight, the reaction mixture was quenched with brine and extracted with ethyl acetate. The combined organic extracts were dried (magnesium sulfate) and concentrated in vacuo to afford the title compound.
Reaction SMILES: C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15]([C:17]1[NH:18][C:19]2[C:24]([CH:25]=1)=[CH:23][C:22]([O:26][CH2:27][CH2:28][O:29][CH3:30])=[CH:21][CH:20]=2)=[O:16])(C)(C)C.NC1C=CC=CC=1NC(C1SC2C=CC(OCCOCCOC)=CC=2C=1)=O>>[NH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15]([C:17]1[NH:18][C:19]2[C:24]([CH:25]=1)=[CH:23][C:22]([O:26][CH2:27][CH2:28][O:29][CH3:30])=[CH:21][CH:20]=2)=[O:16]
Reactant: COCCOc1ccc2[nH]c(C(=O)Nc3ccccc3NC(=O)OC(C)(C)C)cc2c1
Agent: COCCOCCOc1ccc2sc(C(=O)Nc3ccccc3N)cc2c1
Product: COCCOc1ccc2[nH]c(C(=O)Nc3ccccc3N)cc2c1

Procedure:
was prepared: (2-{[5-(2-Methoxy-ethoxy)-1H-indole-2-carbonyl]-amino}-phenyl)-carbamic acid tert-butyl ester (38) in an analogous manner to that described for the preparation of (27) example 11, step 2; exact MW [M+H] calc'd: 326.15; MW found [M+H]: 326.3.
Reaction SMILES: Cl[C:2]1[NH:6][C:5]2[CH:7]=[CH:8][C:9]([C:11]([F:14])([F:13])[F:12])=[CH:10][C:4]=2[N:3]=1.[NH2:15][C:16]1[CH:25]=[CH:24][C:23]2[C:18](=[C:19]([OH:26])[CH:20]=[CH:21][CH:22]=2)[N:17]=1>>[F:12][C:11]([F:14])([F:13])[C:9]1[CH:8]=[CH:7][C:5]2[NH:6][C:2]([O:26][C:19]3[CH:20]=[CH:21][CH:22]=[C:23]4[C:18]=3[N:17]=[C:16]([NH2:15])[CH:25]=[CH:24]4)=[N:3][C:4]=2[CH:10]=1
Reactant: Nc1ccc2cccc(O)c2n1
Reactant: FC(F)(F)c1ccc2[nH]c(Cl)nc2c1
Product: Nc1ccc2cccc(Oc3nc4cc(C(F)(F)F)ccc4[nH]3)c2n1

Procedure:
The reaction of 2-chloro-5-(trifluoromethyl)-1H-benzo[d]imidazole (66 mg, 0.3 mol, prepared according to the procedure described in WO 2004/035549 A1) with 2-amino-8-hydroxyquinoline (48 mg, 0.3 mmol, Fluka) under the condition of Example 1 afforded the title compound as an amorphous solid. MS (ESI, pos. ion) m/z: 345 (M+1).
Reaction SMILES: FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([C:13]([OH:15])=[O:14])=[CH:9][N:8]=1)(=O)=O.[S:18]1[CH:22]=[CH:21][CH:20]=[C:19]1B(O)O.[OH-].[Ba+2].[OH-].COCCOC>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[S:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[C:7]1[CH:12]=[CH:11][C:10]([C:13]([OH:15])=[O:14])=[CH:9][N:8]=1
Reactant: O=C(O)c1ccc(OS(=O)(=O)C(F)(F)F)nc1
Reactant: OB(O)c1cccs1
Agent: [Pd]
Agent: [Ba+2]
Agent: [OH-]
Solvent: O
Solvent: COCCOC
Product: O=C(O)c1ccc(-c2cccs2)nc1

Procedure:
A mixture of 2-trifluoromethanesulfonyloxy-5-pyridinecarboxylic acid (0.442 g, 1.72 mmol), 2-thienylboronic acid (1.56 g, 12.79 mmol), barium hydroxide (0.813 mg, 2.58 mmol), DME (8 mL) and water (1.5 mL) is purged with dry argon. Tetrakis(triphenylphosphine) palladium(0) (99.0 mg, 0.086 mmol) is added, and the resultant solution is stirred at 80° C. for 4 hours. The solvents are evaporated in vacuo, and the residue is partitioned between EtOAc and water. The aqueous extract is separated, and extracted with EtOAc. The organic extracts are combined, washed with sat. aq. NaHCO3 and 5% aq. Na2S2O3, dried, (Na2SO4) and the solvent is evaporated in vacuo. The residue is purified by chromatography to afford the title compound.
Reaction SMILES: [Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH:12]=[CH:13][C:14]3[CH:15]=[C:16]([CH:22]=[CH:23][CH:24]=3)[O:17][CH:18]([CH3:21])[C:19]#[N:20])=[N:9]2)=[CH:4][CH:3]=1.C([Sn]([N:38]=[N+:39]=[N-:40])(CCCC)CCCC)CCC.C(OCC)C.C(O)C>C(Cl)Cl.C(O)(=O)C>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH:12]=[CH:13][C:14]3[CH:15]=[C:16]([CH:22]=[CH:23][CH:24]=3)[O:17][CH:18]([C:19]3[NH:40][N:39]=[N:38][N:20]=3)[CH3:21])=[N:9]2)=[CH:4][CH:3]=1
Reactant: CC(C#N)Oc1cccc(C=Cc2ccc3ccc(Cl)cc3n2)c1
Reactant: CCCC[Sn](CCCC)(CCCC)N=[N+]=[N-]
Solvent: ClCCl
Solvent: CC(=O)O
Solvent: CCO
Product: CC(Oc1cccc(C=Cc2ccc3ccc(Cl)cc3n2)c1)c1nnn[nH]1
Reaction time: 0.5 h

Procedure:
A mixture of the propanonitrile (110 g) from Step 2 and tri-butyltin azide (120 g) was heated at 130° for 3 hours. The residue was dissolved in CH2Cl2 (1 L) on a steam bath. This solution was added to a mixture of diethylether (2 L), ethanol (100 ml) and acetic acid (10 ml). This mixture was evaporated under vacuo to approximately 300 ml. The residue was triturated with ether (1.5 L), ethyl acetate (600 ml) and filtered. The yellow solid was dissolved in 2 N NaOH (150 ml) and H2O (1 L). The aqueous solution was extracted with ethyl acetate (100 ml). The aqueous solution was then acidified with AcOH (100 ml) in ethyl acetate (100 ml). The mixture was stirred 30 min and filtered to give title compound. m.p. 100°-103°.
Reaction SMILES: [CH3:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH:7]([S:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:6]=2[N:5]=[CH:4][CH:3]=1.ClC1C=C(C=CC=1)C(OO)=[O:24]>ClCCl>[CH3:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH:7]([S:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[O:24])[C:6]=2[N:5]=[CH:4][CH:3]=1
Reactant: O=C(OO)c1cccc(Cl)c1
Reactant: Cc1ccnc2c1CCCC2Sc1ccccc1
Solvent: ClCCl
Product: Cc1ccnc2c1CCCC2S(=O)c1ccccc1
Reaction time: 0.5 h
Yield: 101.5 %

Procedure:
A solution of the product of Step 4 (10.0 g, 39.2 mmol) in dichloromethane (200 ml) was treated portionwise with 86% 3-chloroperoxybenzoic acid (8.0 g, 40 mmol) at <10° , stirred for 30 min, washed with 0.1N-NaOH, dried (Na2SO4), and evaporated in vacuo to give the crude product (10.8 g) as a solid.
Reaction SMILES: Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[N:9][CH:8]=[CH:7]2.[CH2:12]([OH:15])[C:13]#[CH:14].C(N(CC)CC)C>ClCCl.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:10]1[C:11]2[C:6](=[CH:5][CH:4]=[CH:3][C:2]=2[C:14]#[C:13][CH2:12][OH:15])[CH:7]=[CH:8][N:9]=1
Reactant: Brc1cccc2ccncc12
Reactant: C#CCO
Agent: Cl[Pd](Cl)([P](c1ccccc1)(c1ccccc1)c1ccccc1)[P](c1ccccc1)(c1ccccc1)c1ccccc1
Solvent: CCN(CC)CC
Solvent: ClCCl
Product: OCC#Cc1cccc2ccncc12
Temperature: 25 °C
Reaction time: 2 h

Procedure:
In an inert atmosphere, 0.068 g of bis(triphenylphosphine)palladium dichloride and 0.013 g of cuprous iodide was added with stirring to a deoxygenated solution of 1 g of 8-bromoisoquinoline, 0.56 mL of propargyl alcohol and 2 mL of triethylamine in 25 mL of dichloromethane. The mixture was stirred at room temperature for 2 hours and then at reflux for 20 hours. The cooled reaction was filtered and the filtrate was concentrated in vacuo. The residual oil was purified by HPLC (ethyl acetate-toluene; 2:3) to yield 0.4 g of 3-(8-isoquinolinyl)-2-propyn-1-ol, mp 138°-139° C.
Reaction SMILES: [CH3:1][S:2]([CH2:5][C:6](=[O:8])[CH3:7])(=[O:4])=[O:3].[Br:9][C:10]1[CH:11]=C[C:13]2[N:18]=[C:17]([CH3:19])OC(=O)[C:14]=2[CH:21]=1.Cl>CN(C)C=O>[Br:9][C:10]1[CH:11]=[C:7]2[C:13](=[CH:14][CH:21]=1)[N:18]=[C:17]([CH3:19])[C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[C:6]2[OH:8]
Reactant: Cc1nc2ccc(Br)cc2c(=O)o1
Reactant: CC(=O)CS(C)(=O)=O
Agent: Cl
Solvent: CN(C)C=O
Product: Cc1nc2ccc(Br)cc2c(O)c1S(C)(=O)=O
Temperature: 100 °C
Reaction time: 0.25 h
Yield: 48.5 %

Procedure:
Methanesulfonylacetone (12.6 g, 92.9 mmol) was dissolved in N,N-dimethylformamide (200 mL) and cooled in ice under nitrogen. Then potassium tert.butylate (11.7 g, 102 mmol) was added (exothermic 20° C.) and stirring without cooling continued for 15 min. Cooled in ice again, then 6-bromo-2-methyl-4H-3,1-benzoxazin-4-one (example B.1) (22.3 g, 92.9 mmol) was added and then stirred without cooling for 4 h. Cooled in ice again, then potassium tert.butylate (11.7 g, 102 mmol) was added, and the resulting red solution was stirred at 20° C. for 15 min and then heated at 100° C. for 30 min. After cooling, 4 M HCl (30 mL) was added, and the mixture was evaporated thoroughly at 0.1 mbar/50° C. The residue was suspended in water (200 mL) and stirred vigorously for 30 min which led to the formation of a filterable precipitate. This solid was filtered off and washed with water (50 mL). One obtained 14.25 g (48.5%) of white crystals. MS: m/z=315/317 (M+H).
Reaction SMILES: [NH2:1][CH2:2][C:3]1([OH:10])[CH2:8][CH2:7][N:6]([CH3:9])[CH2:5][CH2:4]1.S([O-])([O-])(=O)=O.[Mg+2].[CH:17](=O)[CH3:18]>ClCCl>[CH3:17][CH:18]1[NH:1][CH2:2][C:3]2([CH2:8][CH2:7][N:6]([CH3:9])[CH2:5][CH2:4]2)[O:10]1
Reactant: CN1CCC(O)(CN)CC1
Reactant: CC=O
Agent: O=S(=O)([O-])[O-]
Agent: [Mg+2]
Solvent: ClCCl
Product: CC1NCC2(CCN(C)CC2)O1
Temperature: 0 °C
Reaction time: 6 h
Yield: 85.9 %

Procedure:
To a solution of 4-aminomethyl-1-methyl-piperidin-4-ol (2.127 g, 14.77 mmol) in dichloromethane (15 ml) was added anhydrous magnesium sulfate (2.9 g). The resulting mixture was cooled to 0° C. and freshly distilled acetaldehyde (835 μl, 14.78 mmol) was added. After 6 h of stirring at room temperature, the mixture was filtered and the solvent was evaporated under reduced pressure to give the title compound (2.16 g) as an almost colorless liquid. 1H NMR (CDCl3, 500 MHz) δ 4.60 (q, J=5.40 Hz, 1H, CHCH3), 3.01 (d, J=12 Hz, 1H, CHHNH), 2.76 (d, J=12 Hz, 11-1, CHHNH), 2.55-2.31 (m, 4H, CH2N), 2.28 (s, 3H, NCH3), 1.77-1.58 (m, 4H, CH2CO), 1.36 (d, J=5.40 Hz, 3H, CH3CH) ppm; 13C NMR (CDCl3, 300 MHz) δ 87.57 (CH), 57.19 (CH2), 53.14 (C), 52.96 (CH2), 46.15 (CH3), 37.28 (CH2), 35.73 (CH2), 20.32 (CH3) ppm.