2-Bromoethanol → 1-(2-Hydroxyethyl)-4-benzamidopiperidine

HRID 461003Notes

Reaction equation

HRID 461003 reaction equation
[C:1]([NH:9][CH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:17][CH2:18][OH:19].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[OH:19][CH2:18][CH2:17][N:13]1[CH2:14][CH2:15][CH:10]([NH:9][C:1](=[O:8])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:11][CH2:12]1

Participants

5

Reactant 3

HCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 118120N-4-Piperidylbenzamide

Product 1

HCID 203151761-(2-Hydroxyethyl)-4-benzamidopiperidineYield 62.4%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 2.04 grams (0.01 mole) of 4-benzamidopiperidine, 1.25 grams (1 equivalent) of 2-bromoethanol and 2.76 grams (4 equivalents) of potassium carbonate were stirred at 100° C in 2 milliliters of methyl etyl ketone for 2 hours. The mixture was filtered hot and the inorganic residue was washed well with hot methyl ethyl ketone. The filtrate was evaporated to dryness and the resulting white solid recrystallised from ethyl acetate to give 1.55 grams (62%) of 1-(2-hydroxyethyl)-4-benzamidopiperidine.

Workup

  1. filtrationThe mixture was filtered hot
  2. washthe inorganic residue was washed well with hot methyl ethyl ketone
  3. customThe filtrate was evaporated to dryness
  4. customthe resulting white solid recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-39bf0d8a3b844f1e99e9e15a0f6c12df
Source dataset
uspto-grants-1977_12
Patent number
US04061758

Reaction notes

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