2-Fluorobenzoyl chloride → (S)-N-[2-(3,4-Dichloro-phenyl)-4-(2-oxo-[1,4']bipiperidinyl-1'-yl)-butyl]-2-fluoro-N-methyl-benzamide
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:9]([CH2:25][NH:26][CH3:27])[CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][CH:15]([N:18]3[CH2:23][CH2:22][CH2:21][CH2:20][C:19]3=[O:24])[CH2:14][CH2:13]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[F:28][C:29]1[CH:37]=[CH:36][CH:35]=[CH:34][C:30]=1[C:31](Cl)=[O:32]>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]([CH2:10][CH2:11][N:12]2[CH2:13][CH2:14][CH:15]([N:18]3[CH2:23][CH2:22][CH2:21][CH2:20][C:19]3=[O:24])[CH2:16][CH2:17]2)[CH2:25][N:26]([CH3:27])[C:31](=[O:32])[C:30]2[CH:34]=[CH:35][CH:36]=[CH:37][C:29]=2[F:28])[CH:5]=[CH:6][C:7]=1[Cl:8]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To solution of (S)-1′-[3-(3,4-dichloro-phenyl)-4-methylamino-butyl]-[1,4′]bipiperidinyl-2-one (0.3 g) in dichloromethane (7 mL) at 0° C. was added 2-fluorobenzoyl chloride neat. After 45 minutes at ambient temperature, the solution was washed with aqueous sodium bicarbonate, dried and evacuated to an oil which was purified with chromatography, eluting with methanol:dichloromethane (gradient 3:97, 6:94). Concentration to a viscous oil under high vacuum provided the title compound (0.3 g). MS: m/z=534(M+1).