1-Benzyl-4-piperidone → HCID 22768472, compound

HRID 1764464Notes

Reaction equation

HRID 1764464 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][Mg]Cl)=[CH:4][CH:3]=1.[CH2:11]([N:18]1[CH2:23][CH2:22][C:21](=[O:24])[CH2:20][CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Cl-].[NH4+]>C(OCC)C>[CH2:11]([N:18]1[CH2:23][CH2:22][C:21]([CH2:6][C:5]2[CH:9]=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=2)([OH:24])[CH2:20][CH2:19]1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 192201-Benzyl-4-piperidoneHCID 25517Ammonium ChlorideHCID 178478997HCID 178478997, compound

Product 1

HCID 22768472HCID 22768472, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of p-chlorobenzylmagnesium chloride in ethyl ether (prepared from 16 parts of p-chlorobenzyl chloride and 3 parts of magnesium turnings in 100 parts of ethyl ether) is added dropwise a solution of 19 parts of N-benzyl-4-piperidone in 50 parts of ethyl ether, the reaction vessel being cooled in an ice bath during the addition. When the addition is complete, mixture is refluxed for 2 hours, cooled, and the Grignard decomposed with saturated ammonium chloride solution. Evaporation of the ethyl ether gives N-benzyl-4-p-chlorobenzyl-4-hydroxypiperidine. ##STR13##

Workup

  1. temperaturethe reaction vessel being cooled in an ice bath during the addition
  2. additionWhen the addition
  3. temperaturemixture is refluxed for 2 hours
  4. temperaturecooled
  5. customEvaporation of the ethyl ether

Sources & evidence

ORD record
ord-9df930504cde493c91d300ce6569d42b
Source dataset
uspto-grants-1978_09
Patent number
US04116963

Reaction notes

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