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

HRID 1030897Notes

Reaction equation

HRID 1030897 reaction equation
[C:1]1([CH2:7][O:8][C:9]([N:11]2[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][C:19]([OH:21])=O)[CH2:13][CH2:12]2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:24])=O>ClCCl>[Cl:24][C:19](=[O:21])[CH2:18][CH2:17][CH:14]1[CH2:15][CH2:16][N:11]([C:9]([O:8][CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[O:10])[CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 98953153-(1-((Benzyloxy)carbonyl)piperidin-4-yl)propanoic acid

Product 1

HCID 12674069(Phenylmethyl) 4-(3-chloro-3-oxopropyl)-1-piperidinecarboxylateYield 91.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 29 parts of 1-[(phenylmethoxy)carbonyl]-4-piperidinepropanoic acid and 520 parts of dichloromethane were added dropwise 14.9 parts of thionyl chloride. Upon complete addition, stirring was continued overnight at room temperature. The reaction mixture was evaporated, yielding 28.3 parts (91.5%) of (phenylmethyl) 4-(3-chloro-3-oxopropyl)-1-piperidinecarboxylate as a residue (int. 34).

Workup

  1. additionUpon complete addition
  2. customThe reaction mixture was evaporated

Sources & evidence

ORD record
ord-6e8d6cab5dae4a3eadb052a7e0a33ad3
Source dataset
uspto-grants-1992_04
Patent number
US05106973

Reaction notes

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