Oxalyl chloride → Benzyl 4-(chlorocarbonyl)piperidine-1-carboxylate

HRID 71776

Reaction equation

HRID 71776 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17]([OH:19])=O)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C([Cl:23])=O>ClCCl>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17]([Cl:23])=[O:19])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 7364891-Carbobenzoxy-4-piperidinecarboxylic Acid

Product 1

HCID 2776270Benzyl 4-(chlorocarbonyl)piperidine-1-carboxylateYield 101.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Piperidine-1,4-dicarboxylic acid monobenzyl ester (40.2 g, 0.15 mol) in dichloromethane (300 mL) was treated with oxalyl chloride (100 g, 0.79 mol). The reaction mixture was stirred at ambient temperature for 4 hours and the mixture was concentrated to afford crude 4-chlorocarbonyl-piperidine-1-carboxylic acid benzyl ester (43 g), which was used without further purification.

Workup

  1. concentrationthe mixture was concentrated

Sources & evidence

ORD record
ord-a81812e566a8409c8e53a751d6d3ed8c
Source dataset
uspto-grants-2014_09
Patent number
US08822430B2

Linked notes

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