Potassium Hydroxide → HCID 21555723, compound

HRID 267195Notes

Reaction equation

HRID 267195 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][C:34]([C:37]([CH3:40])([CH3:39])[CH3:38])=[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].[OH-].[K+].[BH4-].[K+]>CO>[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][C:34]([C:37]([CH3:40])([CH3:39])[CH3:38])=[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])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 4192641Potassium borohydrideHCID 21555737HCID 21555737, compound

Product 1

HCID 21555723HCID 21555723, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To 8.0 g (0.0143 mole) of 4-[4-[α-(p-tert-butylphenyl) α-hydroxybenzyl]piperidino]-4'-tert-butylbutyrophenone hydrochloride dissolved in 50 ml of methanol is added with stirring a solution of 0.9 g (10% molar excess) of potassium hydroxide in methanol after which 1.54 g of potassium borohydride is added with stirring. The reaction mixture is allowed to react for about 3 hours at room temperature, after which the methanol is removed. Water is added to the remaining residue which is then extracted with ether, dried over magnesium sulfate, and filtered through celite. The filtrate is evaporated under vacuum, and the remaining solid is recrystallized several times from ethanol-water filtering while hot to give 4-[α-(p-tert-butylphenyl)-α-hydroxybenzyl]-α-(p-tert-butylphenyl)-1-piperidinebutanol, M.P. 179°-181.5°C.

Workup

  1. additionis added
  2. additionis added
  3. customto react for about 3 hours at room temperature
  4. customafter which the methanol is removed
  5. additionWater is added to the remaining residue which
  6. extractionis then extracted with ether
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered through celite
  9. customThe filtrate is evaporated under vacuum
  10. customthe remaining solid is recrystallized several times from ethanol-water filtering while hot

Sources & evidence

ORD record
ord-97363133fc8a4dd2a4147c916de66b26
Source dataset
uspto-grants-1976_03
Patent number
US03941795

Reaction notes

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