Thionyl Chloride → HCID 20544988, compound

HRID 2285536Notes

Reaction equation

HRID 2285536 reaction equation
[ClH:1].[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)(O)=[O:3].S(Cl)([Cl:32])=O>CCOCC>[ClH:32].[Cl:1][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)=[O:3]

Participants

4

Reactant 2

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

Product 1

HCID 20544988HCID 20544988, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To 6.0 g of 2-[4-(4-carboxypiperidino)butoxy]bibenzyl hydrochloride was added dropwise 15 ml of thionyl chloride with stirring. The reaction mixture was stirred at room temperature for 3 hours. As the reaction proceeded the reaction mixture became homogenous. Upon completion of the reaction, anhydrous ether was added and the resultant oily product was washed well twice or three times with anhydrous ether. To the washed oil was added anhydrous ether and the mixture was allowed to stand yielding crystalline 2-[4-(4-chlorocarbonylpiperidino)butoxy]bibenzyl hydrochloride which was sufficiently dried for use in the subsequent reaction. To a solution of 10 ml of 50% aqueous dimethylamine solution and 10 ml of tetrahydrofuran cooled in an ice-salt bath was quickly added 1.5 g of crystalline 2-[4-(4-chlorocarbonylpiperidino)butoxy]bibenzyl hydrochloride with stirring. The mixture was allowed to react for 1.5 hours and then concentrated. To the concentrate was added 2 N-NaOH aqueous solution and the product was extracted with ether. The extract from ether was washed with saturated sodium chloride solution and dried over anhydrous sodium sulfate. To the ether solution was added 20% ethanolic hydrogen chloride to yield a precipitate. Recrystallization from ether-ethanol gave 1.2 g (78% yield) of 2-[4-(4-dimethylcarbamoylpiperidino)butoxy]bibenzyl hydrochloride, m.p. 159°-160° C.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 3 hours
  2. additionwas added
  3. washthe resultant oily product was washed well twice
  4. additionTo the washed oil was added anhydrous ether

Sources & evidence

ORD record
ord-2e27e10760f74927b73d5fbc679359c3
Source dataset
uspto-grants-1982_04
Patent number
US04323568

Reaction notes

Loading…