Sodium borohydride → 1-Benzyl-4-(phenylamino)piperidine-4-methanol

HRID 37372Notes

Reaction equation

HRID 37372 reaction equation
[BH4-].[Na+].[C:3]1([NH:9][C:10]2([CH:23]=[O:24])[CH2:15][CH2:14][N:13]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:12][CH2:11]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>CO.O>[C:3]1([NH:9][C:10]2([CH2:23][OH:24])[CH2:15][CH2:14][N:13]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:12][CH2:11]2)[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 19935652HCID 19935652, compound

Product 1

HCID 30172301-Benzyl-4-(phenylamino)piperidine-4-methanolYield 76%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Sodium borohydride (2 g) was added portionwise to a stirred solution of 4-(N-phenylamino)-1-phenylmethyl-piperidine-4-carboxaldehyde (2 g) in methanol at room temperature. After stirring at room temperature for 2 hours the mixture was diluted with water, extracted with chloroform and the combined extracts washed and dried. After removal of the solvent, the crude product was purified by chromatography on silica gel, using chloroform/methanol (38:1) as eluant, to give the title compound (1.53 g) 4-(N-phenylamino)--1-phenylmethyl-4-piperidinylmethanol is then converted to sufentanil following the method described in U.S. Pat. No. 4,179,469 and as illustrated by FIG. 2.

Workup

  1. extractionextracted with chloroform
  2. washthe combined extracts washed
  3. customdried
  4. customAfter removal of the solvent
  5. customthe crude product was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-3f041f1a149f4c3da5afef44e7d0f088
Source dataset
uspto-grants-1995_05
Patent number
US05420280

Reaction notes

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