Dimethylformamide → 1-phenyl-7-[4-(2-propoxyethoxy)phenyl]-N-[4-[[N-methyl-N-(tetrahydro-2H-pyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide hydrochloride

Reaction equation

[C:1]1([N:7]2[C:13]3[CH:14]=[CH:15][C:16]([C:18]4[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][O:27][CH2:28][CH2:29][CH3:30])=[CH:20][CH:19]=4)=[CH:17][C:12]=3[CH:11]=[C:10]([C:31](O)=[O:32])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:36])=O.[CH3:38][N:39]([CH:41]=O)[CH3:40]>>[ClH:36].[C:1]1([N:7]2[C:13]3[CH:14]=[CH:15][C:16]([C:18]4[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][O:27][CH2:28][CH2:29][CH3:30])=[CH:20][CH:19]=4)=[CH:17][C:12]=3[CH:11]=[C:10]([C:31]([NH:7][C:1]3[CH:6]=[CH:5][C:4]([CH2:41][N:39]([CH3:38])[CH:40]4[CH2:26][CH2:25][O:24][CH2:21][CH2:20]4)=[CH:3][CH:2]=3)=[O:32])[CH2:9][CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Reactant 3

HCID 6228Dimethylformamide

HCID 24386Thionyl Chloride

HCID 223289381-phenyl-7-[4-(2-propoxyethoxy)phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxylic acid

Product 1

HCID 223289571-phenyl-7-[4-(2-propoxyethoxy)phenyl]-N-[4-[[N-methyl-N-(tetrahydro-2H-pyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide hydrochloride

Procedure

In DMF (6 ml) was dissolved 1-phenyl-7-[4-(2-propoxyethoxy)phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxylic acid (0.2 g). Under ice-cooling, to the mixture was added thionyl chloride (0.08 ml). The mixture was stirred at room temperature for 30 minutes. The solvent was evaporated under reduced pressure. In THF (20 ml) was suspended the residue, the suspension was added dropwise to a solution of 4-[N-methyl-N-(tetrahydro-2H-pyran-4-yl)aminomethyl]aniline (0.12 g) and triethylamine (0.31 ml) in THF (5 ml), under ice-cooling. The mixture was stirred at room temperature overnight under nitrogen atmosphere. The solvent was evaporated under reduced pressure. Water was added to the mixture, the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried with anhydrous magnesium sulfate. The solvent was evaporated, the residue was purified with silica gel column chromatography (ethyl acetate/methanol/triethylamine), which was dissolved in ethyl acetate-ethanol, 4N hydrochloric acid-ethyl acetate was added to the solution, and the solvent was evaporated to give 1-phenyl-7-[4-(2-propoxyethoxy)phenyl]-N-[4-[[N-methyl-N-(tetrahydro-2H-pyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide hydrochloride (Compound 38) (0.17 g) as yellow crystals.