Potassium Hydroxide → 4-(3,4-Dichlorophenyl)-4-piperidinol

HRID 5155Notes

Reaction equation

HRID 5155 reaction equation
C(OC([N:6]1[CH2:11][CH2:10][C:9]([OH:20])([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=2)[CH2:8][CH2:7]1)=O)C.[OH-].[K+]>C(O)CCC>[OH:20][C:9]1([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=2)[CH2:10][CH2:11][NH:6][CH2:7][CH2:8]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 20077503Ethyl 4-(3,4-dichlorophenyl)-4-hydroxypiperidine-1-carboxylate

Product 1

HCID 186757284-(3,4-Dichlorophenyl)-4-piperidinolYield 90%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 64.2 g of 1-ethoxycarbonyl-4-hydroxy-4-(3,4-dichlorophenyl)piperidine (X-1) and a solution of 72.4 g of KOH in 700 ml of nBuOH is refluxed for 2 hours and evaporated. The reaction mixture is concentrated under reduced pressure and extracted with ethyl acetate. The organic layer is washed with water, dried and evaporated. The resulting crystalline residue is recrystallized from ethyl acetate to prepare 44.7 g (Yield: 90.0%) of the compound (II-1). mp. 144.5°-146.0° C.

Workup

  1. customevaporated
  2. concentrationThe reaction mixture is concentrated under reduced pressure
  3. extractionextracted with ethyl acetate
  4. washThe organic layer is washed with water
  5. customdried
  6. customevaporated
  7. customThe resulting crystalline residue is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-0d60770bcb50476997f7e87cec0a58de
Source dataset
uspto-grants-1993_09
Patent number
US05243051

Reaction notes

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