Azzindani/Open_Reaction_Data huggingface dataset:
Reaction SMILES: [CH2:1]1[C@@H:10]2[C@H:5]([CH2:6][CH2:7][C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=32)[CH2:4][NH:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C=O)C>[CH2:22]([N:3]1[CH2:2][CH2:1][C@@H:10]2[C@H:5]([CH2:6][CH2:7][C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=32)[CH2:4]1)[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1
Reactant: BrCCc1ccccc1
Reactant: c1ccc2c(c1)CC[C@@H]1CNCC[C@@H]21
Agent: O=C([O-])[O-]
Agent: [K+]
Solvent: CN(C)C=O
Product: c1ccc(CCN2CC[C@H]3c4ccccc4CC[C@@H]3C2)cc1
Yield: 25.1 %

Procedure:
Following the procedure of Example 3, step 4, 0.307 g (1.64 mmol) of crude trans-1,2,3,4,4a,5,6,10b-octahydrobenz[f]isoquinoline in 8 ml of anhydrous DMF was reacted with 0.249 g (1.80 mmol) of anhydrous potassium carbonate and 0.222 ml (1.64 mmol) of (2-bromoethyl)benzene. Chromatography on flash silica, eluting with 20-50% ethyl acetate/petroleum ether, gave 0.12 g (25%) of the title product as a colourless oil. The hydrochloride salt was made using ethereal hydrogen chloride. Upon evaporation of the solvent the title product hydrochloride was obtained as a white solid, m.p. 277°-283° C. (dec). NMR δ(D2O) 1.54-1.92 (4H, m), 2.72 (2H, m), 2.93-3.00 (3H, m), 3.13-3.26 (3H, m), 3.46 (2H, t), 3.71 (1H, m), 3.84 (1H, m), 7.24-7.28 (3H, m), 7.37-7.44 (6H, m). m/z (CI+, NH3) 292 (M+H)+, 200 (M-CH2Ph)+. Analysis calcd. for C21H26ClN: C, 76.92; H, 7.99; N, 4.27%. Found: C, 76.94; H, 7.98; N, 4.44%.
Reaction SMILES: [ClH:1].O1CCOCC1.[F:8][C:9]1[CH:10]=[C:11]([CH:44]=[CH:45][CH:46]=1)[CH2:12][O:13][C:14]1[CH:43]=[CH:42][C:17]([O:18][CH:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]3[CH:29]=[N:30][CH:31]=[C:32]([NH:34]C(OC(C)(C)C)=O)[CH:33]=3)=[O:26])[CH2:21][CH2:20]2)=[CH:16][CH:15]=1>C1COCC1>[ClH:1].[F:8][C:9]1[CH:10]=[C:11]([CH:44]=[CH:45][CH:46]=1)[CH2:12][O:13][C:14]1[CH:43]=[CH:42][C:17]([O:18][C:19]2[CH:20]=[CH:21][N:22]([C:25]([O:27][CH:28]3[CH2:33][CH:32]([NH2:34])[CH2:31][NH:30][CH2:29]3)=[O:26])[CH2:23][CH:24]=2)=[CH:16][CH:15]=1
Reactant: CC(C)(C)OC(=O)Nc1cncc(OC(=O)N2CCC(Oc3ccc(OCc4cccc(F)c4)cc3)CC2)c1
Agent: Cl
Solvent: C1COCCO1
Solvent: C1CCOC1
Product: NC1CNCC(OC(=O)N2C=CC(Oc3ccc(OCc4cccc(F)c4)cc3)=CC2)C1
Temperature: 60 °C
Reaction time: 4 h

Procedure:
A 4 M hydrogen chloride/dioxane solution (1.8 ml) was added to a THF (10 ml) solution containing 5-[(tert-butoxycarbonyl)amino]pyridin-3-yl 4-{4-[(3-fluorobenzyl)oxy]phenoxy}piperidine-1-carboxylate (174 mg), followed by stirring at 60° C. for 4 hours. The solvent was evaporated under reduced pressure to obtain 5-aminopiperidin-3-yl 4-{4-[(3-fluorobenzyl)oxy]phenoxy}pyridine-1-carboxylate hydrochloride (74 mg).
Reaction SMILES: [N+:1]([C:4]1[CH:25]=[CH:24][C:7]([C:8]([N:10]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[CH2:14][N:13]3[N:21]=[CH:22][CH:23]=[C:12]3[CH2:11]2)=[O:9])=[CH:6][CH:5]=1)([O-])=O.NN>C(O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:8]([N:10]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[CH2:14][N:13]3[N:21]=[CH:22][CH:23]=[C:12]3[CH2:11]2)=[O:9])=[CH:24][CH:25]=1
Reactant: O=C(c1ccc([N+](=O)[O-])cc1)N1Cc2ccnn2Cc2ccccc21
Agent: [Pd]
Agent: NN
Solvent: CCO
Product: Nc1ccc(C(=O)N2Cc3ccnn3Cc3ccccc32)cc1

Procedure:
To a solution of 5 mmol of 5,10-dihydro-5-(4-nitrobenzoyl)-4H-pyrazolo-[5,1-c][1,4]benzodiazepine in 25 ml of ethyl alcohol is added 0.3 g of 10% Pd/C and 15 mmol of hydrazine. The mixture is heated under reflux for 3 hours, and the mixture is filtered through diatomaceous earth. The filtrate is concentrated in vacuo to a residue which is dissolved in methylene chloride and passed through a thin pad of hydrous magnesium silicate. The filtrate is concentrated in vacuo to give the desired product which is purified by flash chromatography on silica gel to give the desired product as a solid, exact mass by mass spectrometry: 305.1402(M+H) .
Reaction SMILES: [Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3[CH:13]=[CH:14][C:15]([CH2:17][CH2:18][CH2:19][CH2:20]O)=[CH:16][C:11]=3[S:10][N:9]=2)=[CH:4][CH:3]=1.[CH3:22][NH:23][CH3:24]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3[CH:13]=[CH:14][C:15]([CH2:17][CH2:18][CH2:19][CH2:20][N:23]([CH3:24])[CH3:22])=[CH:16][C:11]=3[S:10][N:9]=2)=[CH:4][CH:3]=1
Reactant: OCCCCc1ccc2c(-c3ccc(Br)cc3)nsc2c1
Reactant: CNC
Product: CN(C)CCCCc1ccc2c(-c3ccc(Br)cc3)nsc2c1

Procedure:
In analogy to example 19.1, 4-[3-(4-Bromo-phenyl)-benzo[d]isothiazol-6-yl]-butan-1-ol and Dimethylamine were converted to yield {4-[3-(4-Bromo-phenyl)-benzo[d]isothiazol-6-yl]-butyl}-dimethyl-amine as brown oil, MS: 389 (MH+, 1Br).
Reaction SMILES: [C:1]1([CH:7]2[O:12][C@H:11]3[CH2:13][C@H:14]([OH:17])[CH2:15][O:16][C@@H:10]3[CH2:9][O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:18][S:19](Cl)(=[O:21])=[O:20]>CN(C1C=CN=CC=1)C.N1C=CC=CC=1.C1(C)C=CC=CC=1>[CH3:18][S:19]([O:17][C@@H:14]1[CH2:15][O:16][C@H:10]2[C@@H:11]([O:12][CH:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[O:8][CH2:9]2)[CH2:13]1)(=[O:21])=[O:20]
Reactant: CS(=O)(=O)Cl
Reactant: O[C@@H]1CO[C@@H]2COC(c3ccccc3)O[C@H]2C1
Agent: CN(C)c1ccncc1
Solvent: c1ccncc1
Solvent: Cc1ccccc1
Product: CS(=O)(=O)O[C@@H]1CO[C@@H]2COC(c3ccccc3)O[C@H]2C1
Temperature: 0 °C
Reaction time: 1.5 h

Procedure:
To a stirred solution of (4aR,7S,8aS)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-7-ol (850 mg, 3.60 mmol) and DMAP (22 mg, 0.180 mmol) under nitrogen in anhydrous pyridine (10.0 mL) at 0° C. was added methanesulfonyl chloride (0.51 mL, 742 mg, 6.48 mmol) dropwise over 2 minutes. After stirring at 0° C. for 1.5 hours, the mixture was diluted with toluene (10 mL) and concentrated under reduced pressure. The resultant white solid was dissolved in DCM and filtered to remove solids. The filtrate was then chromatographed using a Biotage™ 50 g silica gel cartridge eluted with 0-50% EtOAc in 1:1 Hexane/DCM over 20 column volumes. The product fractions were combined and concentrated under reduced pressure to provide the title compound as a white solid. LC-MS: calculated for C14H18O6S 314.08, observed m/e: 315.06 (M+H)+ (Rt 1.56/4 min).
Reaction SMILES: [Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH2:10]O)[CH:5]=[N:6][CH:7]=1.S(Cl)([Cl:14])=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH2:10][Cl:14])[CH:5]=[N:6][CH:7]=1
Reactant: OCC=Cc1cncc(Br)c1
Reactant: O=S(Cl)Cl
Agent: O=C([O-])O
Agent: [Na+]
Solvent: ClCCl
Product: ClCC=Cc1cncc(Br)c1
Yield: 76 %

Procedure:
A solution of 3-(5-bromo-3-pyridinyl)prop-2-en-1-ol (0.85 gms, 3.97 mmol) is diluted with methylene chloride (20 mls). Thionyl chloride (0.27 mls, 97%, leq) is added at room temperature. After one hour a second equivalent of thionyl chloride is added. The reaction is neutralized with saturated aqueous NaHCO3 after an additional hour and extracted with methylene chloride. The organic layer is dried over Na2SO4 and evaporated to yield 0.70 gms of an oil (76%). 1H NMR (CDCl3, 300 MHz) δ8.90 (s, 1H), 8.70 (s, 1H), 8.40 (s, 1H), 6.70 (m, 2H), and 4.30 (d, J=3.8 Hz, 2H).
Reaction SMILES: [N:1]([CH2:4][CH2:5][NH2:6])=[N+:2]=[N-:3].C(N(CC)CC)C.[C:14](Cl)(=[O:28])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]>C(Cl)Cl>[N:1]([CH2:4][CH2:5][NH:6][C:14](=[O:28])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[N+:2]=[N-:3]
Reactant: CCCCCCCCCCCCCC(=O)Cl
Reactant: [N-]=[N+]=NCCN
Solvent: ClCCl
Solvent: CCN(CC)CC
Product: CCCCCCCCCCCCCC(=O)NCCN=[N+]=[N-]
Temperature: 25 °C
Reaction time: 24 h
Yield: 70 %

Procedure:
To a 25 mL round-bottomed flask equipped with a magnetic stir bar was added 2-azidoethanamine (0.102 g, 1.18 mmol), DCM (5 mL) and then triethylamine (0.239 g, 2.37 mmol). To this reaction mixture, tetradecanoyl chloride (0.292 g, 1.18 mmol) was added dropwise and allowed to stir at room temperature for 24 hr. Then, the reaction mixture was concentrated de vacuo and then purified via silica gel column chromatography (100% dichloromethane to 1:40 methanol:dichloromethane) to give N-(2-azidoethyl)tetradecanamide (0.245 g, 79% yield). 1H NMR (300 MHz, CDCl3) δ 5.86 (s, 1H), δ 3.42 (s, 41-1), δ 2.18 (t, J=7.8 Hz, 2H), δ 1.62 (m, 2H), δ 1.24 (m, 20H), δ 0.87 (t, J=3.9 Hz, 3H) ppm; 13C NMR (75 MHz, CDCl3) δ 173.7, 51.2, 39.1, 36.9, 32.1, 29.9, 29.8, 29.7, 29.6, 29.5, 25.9, 22.9, 14.4 ppm; HRMS (ESI) calcd for C16H32N4O (M+) 296.2576. found 296.2566.