Oxalyl chloride → 1-Methylpiperidine-4-carbonyl chloride hydrochloride

HRID 245714

Reaction equation

HRID 245714 reaction equation
[ClH:1].[CH3:2][N:3]1[CH2:8][CH2:7][CH:6]([C:9](O)=[O:10])[CH2:5][CH2:4]1.C(Cl)(=O)C([Cl:15])=O>ClCCl.CN(C)C=O>[ClH:15].[CH3:2][N:3]1[CH2:8][CH2:7][CH:6]([C:9]([Cl:1])=[O:10])[CH2:5][CH2:4]1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 27600434-Piperidinecarboxylic acid, 1-methyl-, hydrochloride (1:1)

Product 1

HCID 219565061-Methylpiperidine-4-carbonyl chloride hydrochlorideYield 111.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 1-methyl-piperidine-4-carboxylic acid hydrochloride (11.36 mmol, 2.04 g) and N,N-dimethylformamide (0.129 mmol, 0.01 ml, 9.40 mg) in dichloromethane (10 ml) at 0° C. was added oxalyl chloride (14.76 mmol, 1.40 ml) drop wise. The cooling bath was removed and the reaction mixture stirred at room temperature for 20 hours. Then the reaction mixture was concentrated in vacuo to give 1-methylpiperidine-4-carbonyl chloride hydrochloride (2.5 g).

Workup

  1. customThe cooling bath was removed
  2. concentrationThen the reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-5c63cbcfa90a49bcbd1a3c66ee2477c2
Source dataset
uspto-grants-2014_02
Patent number
US08658794B2

Linked notes

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