Sodium borohydride → 1-(4-Aminobenzoyl)-4-[(4-fluorophenyl)hydroxymethyl]piperidine
Reaction equation
[BH4-].[Na+].[NH2:3][C:4]1[CH:26]=[CH:25][C:7]([C:8]([N:10]2[CH2:15][CH2:14][CH:13]([C:16](=[O:24])[C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[CH2:12][CH2:11]2)=[O:9])=[CH:6][CH:5]=1>CO>[NH2:3][C:4]1[CH:5]=[CH:6][C:7]([C:8]([N:10]2[CH2:11][CH2:12][CH:13]([CH:16]([C:17]3[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=3)[OH:24])[CH2:14][CH2:15]2)=[O:9])=[CH:25][CH:26]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Sodium borohydride (0.058 g) was added to a solution of 1-(4-aminobenzoyl)-4-(4-fluorobenzoyl)piperidine (1.0 g) in methanol (80 ml) and the mixture was stirred at room temperature for 2 hours. Additional sodium borohydride (0.050 g) was added. After being stirred at the same temperature for 1.5 hours, the resultant mixture was concentrated in vacuo. The residue was diluted with water and extracted twice with methylene chloride. The extracts were combined, washed with brine, dried over magnesium sulfate, and concentrated to dryness in vacuo. The powdery residue was washed with diisopropyl ether to give 1-(4-aminobenzoyl)-4-[(4-fluorophenyl)hydroxymethyl]piperidine (1.00 g) as pale yellow powder.