Ethanol → 2-[4-(4-Ethoxycarbonylpiperidino)butoxy]bibenzyl hydrochloride

HRID 27059Notes

Reaction equation

HRID 27059 reaction equation
Cl.[C:2]([CH:5]1[CH2:10][CH2:9][N:8]([CH2:11][CH2:12][CH2:13][CH2:14][O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:7][CH2:6]1)([OH:4])=[O:3].S(Cl)([Cl:32])=O.[CH2:34](O)[CH3:35]>>[ClH:32].[CH2:34]([O:3][C:2]([CH:5]1[CH2:10][CH2:9][N:8]([CH2:11][CH2:12][CH2:13][CH2:14][O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH2:22][CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:7][CH2:6]1)=[O:4])[CH3:35]

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 30553444-Piperidinecarboxylic acid, 1-(4-(2-(2-phenylethyl)phenoxy)butyl)-, hydrochloride

Product 1

HCID 205450082-[4-(4-Ethoxycarbonylpiperidino)butoxy]bibenzyl hydrochlorideYield 87%

Procedure

To a solution of 3 g of 2-[4-(4-carboxypiperidino)butoxy]bibenzyl hydrochloride in 30 ml of ethanol was added dropwise 0.9 g of thionyl chloride. The reaction mixture was stirred for one hour, heated under reflux for 30 minutes, concentrated in vacuo and then recrystallized from ethanolether to give 2.8 g (87% yield) of 2-[4-(4-ethoxycarbonylpiperidino)butoxy]bibenzyl hydrochloride, m. p. 84°-87° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 30 minutes
  3. concentrationconcentrated in vacuo
  4. customrecrystallized from ethanolether

Sources & evidence

ORD record
ord-5f07fd8899e14afd9f3ec1f1a935fa8f
Source dataset
uspto-grants-1980_09
Patent number
US04220603

Reaction notes

Loading…