Thionyl Chloride → Ethyl 4-(3-chloropropyl)-1-piperidinecarboxylate

HRID 1030905Notes

Reaction equation

HRID 1030905 reaction equation
O[CH2:2][CH2:3][CH2:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:7][CH2:6]1.S(Cl)([Cl:18])=O>C1C=CC=CC=1>[Cl:18][CH2:2][CH2:3][CH2:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 14989198Ethyl 4-(3-hydroxypropyl)piperidine-1-carboxylate

Product 1

HCID 14989201Ethyl 4-(3-chloropropyl)-1-piperidinecarboxylateYield 83.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a stirred mixture of 36 parts of ethyl 4-(3-hydroxypropyl)-1-piperidinecarboxylate and 261 parts of benzene were added dropwise 21.5 parts of thionyl chloride at 5°-10° C. Upon complete addition, stirring was continued overnight at this temperature. The reaction mixture was evaporated and the residue was taken up in methylbenzene. The solvent was evaporated (this was repeated twice), yielding 33 parts (83.8%) of ethyl 4-(3-chloropropyl)-1-piperidinecarboxylate as a residue (int. 58).

Workup

  1. additionUpon complete addition
  2. customThe reaction mixture was evaporated
  3. customThe solvent was evaporated (

Sources & evidence

ORD record
ord-238147e020794d1c85a4f20f58a07681
Source dataset
uspto-grants-1992_04
Patent number
US05106973

Reaction notes

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