Oxalyl chloride → 1-(4-Nitrophenyl)piperidine-4-carboxylic acid chloride hydrochloride

HRID 2236832Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][CH:13]([C:16]([OH:18])=O)[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(Cl)(=O)C([Cl:22])=O>ClCCl.CN(C)C=O>[ClH:22].[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][CH:13]([C:16]([Cl:22])=[O:18])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

Conditions

Temperature: 60 °C

Procedure

To a suspension of 1-(4-nitrophenyl)piperidine-4-carboxylic acid (0.75 g, 3.0 mmol) in dichloromethane (15 mL) is added oxalyl chloride (0.32 mL, 3.6 mmol) and then one drop of N,N-dimethylformamide. The reaction mixture is heated in a 60° C. oil bath under a nitrogen atmosphere for 30 minutes, concentrated under reduced pressure to provide 1-(4-nitrophenyl)piperidine-4-carboxylic acid chloride hydrochloride. N,N-dimethylethylenediamine (1.0 mmol) is added neat to 1-(4-nitrophenyl)piperidine-4-carboxylic acid chloride hydrochloride (0.15 g, 0.5 mmol). The resulting solid is purified by reverse-phase HPLC to provide 1-(4-nitro-phenyl)-piperidine-4-carboxylic acid (2-dimethylamino-ethyl)-amide trifluoroacetate.

Workup

concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-13a563752e8647f488e9905d3decd764
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07713994B2

Reaction notes

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