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

HRID 484484Notes

Reaction equation

HRID 484484 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-piperdinepropanoic 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-a5e93ec437af438da15cc6fc3d6e5d05
Source dataset
uspto-grants-1993_07
Patent number
US05231184

Reaction notes

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