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

HRID 981616Notes

Reaction equation

HRID 981616 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-069448fc98604a0e8433057da4635f8a
Source dataset
uspto-grants-1991_02
Patent number
US04992433

Reaction notes

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