Potassium Hydroxide → HCID 21552967, compound

HRID 267978Notes

Reaction equation

HRID 267978 reaction equation
Cl.[C:2]([C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:37])[CH2:13][CH2:14][CH2:15][CH2:16][N:17]2[CH2:22][CH2:21][CH:20]([C:23]([OH:36])([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:19][CH2:18]2)=[CH:8][CH:7]=1)([CH3:5])([CH3:4])[CH3:3].[OH-].[K+].[BH4-].[Na+]>CO>[C:2]([C:6]1[CH:7]=[CH:8][C:9]([CH:12]([OH:37])[CH2:13][CH2:14][CH2:15][CH2:16][N:17]2[CH2:22][CH2:21][CH:20]([C:23]([OH:36])([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:19][CH2:18]2)=[CH:10][CH:11]=1)([CH3:5])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 4311764Sodium borohydrideHCID 21552950HCID 21552950, compound

Product 1

HCID 21552967HCID 21552967, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 62.3 g (0.12 mole) of 4'-tert-butyl-5-[4-(α-hydroxy-α-phenylbenzyl)piperidino]valerophenone hydrochloride dissolved in about 1200 ml of methanol is added methanolic potassium hydroxide until the solution is basic. The solution is cooled in an ice bath with stirring and 5 g (0.13 mole) of sodium borohydride is added portionwise. The mixture is stirred an additional half hour, allowed to warm to room temperature then heated on a steam bath for half an hour. The solvent is removed at reduced pressure and the remaining residue is washed with water and recrystallized from acetone to give α-(p-tert-butylphenyl)-4-(α-hydroxy-α-phenylbenzyl)-1-piperidine-pentanol.

Workup

  1. temperatureThe solution is cooled in an ice bath
  2. stirringThe mixture is stirred an additional half hour
  3. temperaturethen heated on a steam bath for half an hour
  4. customThe solvent is removed at reduced pressure
  5. washthe remaining residue is washed with water
  6. customrecrystallized from acetone

Sources & evidence

ORD record
ord-df67968109384b588019d993272192fe
Source dataset
uspto-grants-1976_03
Patent number
US03946022

Reaction notes

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