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Potassium borohydride → 4-[alpha-(p-Tert-butylphenyl)-alpha-hydroxybenzyl]-alpha-phenyl-1-piperidinebutanol

HRID 267193
Notes
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Reaction equation

HRID 267193 reaction equation
Cl.[C:2]([C:6]1[CH:11]=[CH:10][C:9]([C:12]([CH:20]2[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][CH2:28][C:29]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[O:30])[CH2:22][CH2:21]2)([OH:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:8][CH:7]=1)([CH3:5])([CH3:4])[CH3:3].C[O-].[Na+].[BH4-].[K+]>CO.O>[C:2]([C:6]1[CH:7]=[CH:8][C:9]([C:12]([CH:20]2[CH2:21][CH2:22][N:23]([CH2:26][CH2:27][CH2:28][CH:29]([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[OH:30])[CH2:24][CH2:25]2)([OH:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:10][CH:11]=1)([CH3:5])([CH3:3])[CH3:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 4192641Potassium borohydrideHCID 10942334Sodium MethoxideHCID 215557314-[4-[alpha-(p-Tert-butylphenyl)-alpha-hydroxybenzyl]piperidino]butyrophenone hydrochloride

Product 1

HCID 215557154-[alpha-(p-Tert-butylphenyl)-alpha-hydroxybenzyl]-alpha-phenyl-1-piperidinebutanol

Reagents, catalysts & solvents 2

HCID 887
Methanol
Solvent
HCID 962WaterSolvent

Procedure

To a mixture of 4.2 g (0.0083 mole) of 4-[4-[α-(p tert-butylphenyl)-α-hydroxybenzyl]piperidino]butyrophenone hydrochloride and 0.54 g (0.01 mole) of sodium methoxide in 25 ml of methanol is added 2.16 g (0.04 mole) of potassium borohydride. The reaction mixture is stirred overnight, diluted with water and the methanol removed under reduced pressure. The remaining material is extracted with chloroform, washed with water, dried over magnesium sulfate and filtered. The filtrate is concentrated, and the residue is recrystallized from acetone-water to give 4-[α-(p-tert-butylphenyl)-α-hydroxybenzyl]-α-phenyl-1-piperidinebutanol, M.P. 161°-163°C.

Workup

  1. customthe methanol removed under reduced pressure
  2. extractionThe remaining material is extracted with chloroform
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate is concentrated
  7. customthe residue is recrystallized from acetone-water

Sources & evidence

ORD record
ord-31d54994f1804563936e334fbdce7530
Source dataset
uspto-grants-1976_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US03941795

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes