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]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
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
- customthe methanol removed under reduced pressure
- extractionThe remaining material is extracted with chloroform
- washwashed with water
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationThe filtrate is concentrated
- customthe residue is recrystallized from acetone-water
Sources & evidence
- ORD record
- ord-31d54994f1804563936e334fbdce7530
- Source dataset
- uspto-grants-1976_03
- Patent number
- US03941795
Linked notes
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