Sodium borohydride → 1-(4-Aminobenzoyl)-4-[(4-fluorophenyl)hydroxymethyl]piperidine

HRID 648509Notes

Reaction equation

HRID 648509 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]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydride2×HCID 136039661-(4-Aminobenzoyl)-4-(4-fluorobenzoyl)piperidine

Product 1

HCID 138250431-(4-Aminobenzoyl)-4-[(4-fluorophenyl)hydroxymethyl]piperidineYield 99.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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.

Workup

  1. stirringAfter being stirred at the same temperature for 1.5 hours
  2. concentrationthe resultant mixture was concentrated in vacuo
  3. additionThe residue was diluted with water
  4. extractionextracted twice with methylene chloride
  5. washwashed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated to dryness in vacuo
  8. washThe powdery residue was washed with diisopropyl ether

Sources & evidence

ORD record
ord-a394553276f946d88c4b85415d94a60f
Source dataset
uspto-grants-1988_04
Patent number
US04735952

Reaction notes

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