Ammonia → 1-(tert-Butoxycarbonyl)piperidine-4-carboxamide

HRID 1351413Notes

Reaction equation

ClC(OCC)=O.[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][CH:17]([C:20]([OH:22])=O)[CH2:16][CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8].C([N:25](CC)CC)C.N>ClCCl>[NH2:25][C:20]([CH:17]1[CH2:18][CH2:19][N:14]([C:12]([O:11][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:13])[CH2:15][CH2:16]1)=[O:22]

Participants

Conditions

Temperature: 0 °C

Procedure

Ethyl chloroformate (4.6 ml, 48.3 mmol) was added slowly to a solution of 1-(tert-butoxycarbonyl)4-piperidinecarboxylic acid (10 g, 43.6 mmol) in dichloromethane (100 ml) stirred at 0° C. Triethylamine (7.6 ml, 52.3 mmol) was added with stirring over two minutes. 0.88 Ammonia solution (40 ml) was added and the mixture allowed to warm to room temperature with stirring. The mixture was washed with water, 1M citric acid solution and brine, dried (MgSO4), filtered and evaporated under reduced pressure gave the title compound as white solid, 8.94 g.

Workup

stirringwith stirring over two minutes
temperatureto warm to room temperature
stirringwith stirring
washThe mixture was washed with water, 1M citric acid solution and brine
dry with materialdried (MgSO4)
filtrationfiltered
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-e92e786ce4ae406fadd39dc142270641
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07217714B1

Reaction notes

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