Oxalyl chloride → tert-Butyl 4-(Chlorocarbonyl)piperidine-1-carboxylate

Reaction equation

[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=O)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(Cl)(=O)C([Cl:20])=O>>[C:4]([O:3][C:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([Cl:20])=[O:16])[CH2:10][CH2:9]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

Reactant 2

HCID 65578Oxalyl chloride

HCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acid

Product 1

HCID 21906247tert-Butyl 4-(Chlorocarbonyl)piperidine-1-carboxylate

Procedure

1-Boc-piperidine-4-carboxylic acid (4.4 g, 19.2 mmol) in oxalyl chloride (50 mL) was heated at reflux for 3 h and then concentrated and dried in vacuo to give the acid chloride, 4-chlorocarbonyl-piperidine-1-carboxylic acid tert-butyl ester.

Workup

temperatureat reflux for 3 h
concentrationconcentrated
customdried in vacuo

Sources & evidence

ORD record: ord-2c8672fdeb6341d192fb145e1d845f08
Source dataset: uspto-grants-2005_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06974870B2

Reaction notes

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