Thionyl Chloride → Ethyl 4-(3-chloro-3-oxopropyl)-1-piperidinecarboxylate

HRID 981619Notes

Reaction equation

HRID 981619 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][CH:9]([CH2:12][CH2:13][C:14]([OH:16])=O)[CH2:8][CH2:7]1)=[O:5])[CH3:2].S(Cl)([Cl:19])=O>ClC(Cl)Cl>[Cl:19][C:14](=[O:16])[CH2:13][CH2:12][CH:9]1[CH2:10][CH2:11][N:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:7][CH2:8]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 149891953-(1-(Ethoxycarbonyl)piperidin-4-yl)propanoic acid

Product 1

HCID 14989196Ethyl 4-(3-chloro-3-oxopropyl)-1-piperidinecarboxylateYield 47%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred mixture of 200 parts of 1-(ethoxycarbonyl)-4-piperidinepropanoic acid and 750 parts of trichloromethane were added 320 parts of thionyl chloride. The whole was stirred for 18 hours at room temperature. The reaction mixture was evaporated with methylbenzene. The residue was distilled, yielding 102.6 parts (47%) of ethyl 4-(3-chloro-3-oxopropyl)-1-piperidinecarboxylate; bp. 165-170 at 399 Pa (int. 45).

Workup

  1. customThe reaction mixture was evaporated with methylbenzene
  2. distillationThe residue was distilled

Sources & evidence

ORD record
ord-4ef05e2268014532bda894b397d622e2
Source dataset
uspto-grants-1991_02
Patent number
US04992433

Reaction notes

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