Thionyl Chloride → 1-(2-Chloroethyl)-4-benzamidopiperidine

HRID 461004Notes

Reaction equation

HRID 461004 reaction equation
O[CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][CH:7]([NH:10][C:11](=[O:18])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:6][CH2:5]1.S(Cl)([Cl:21])=O>C1C=CC=CC=1>[Cl:21][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][CH:7]([NH:10][C:11](=[O:18])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:6][CH2:5]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 203151761-(2-Hydroxyethyl)-4-benzamidopiperidine

Product 1

HCID 213952311-(2-Chloroethyl)-4-benzamidopiperidine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

1 Gram of 1-(2-hydroxyethyl)-4-benzamidopiperidine suspended in 2 milliliters of dry benzene was treated with 0.62 gram of thionyl chloride. The stirred mixture was refluxed for 3 hours., then cooled and filtered to give the title compound as a light grey solid. Crystallisation from ethanol-ether of this hydrochloride gave 0.8 grams (62%) of pale yellow needles, melting point 238.5° C.

Workup

  1. temperatureThe stirred mixture was refluxed for 3 hours
  2. temperature, then cooled
  3. filtrationfiltered

Sources & evidence

ORD record
ord-580ea0ec41dd4e928347c076d7ee6ae6
Source dataset
uspto-grants-1977_12
Patent number
US04061758

Reaction notes

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