Ammonia → 1H-benzo[d]imidazol-2-ylsulfonyl-2-piperidinecarboxamide

HRID 397653Notes

Reaction equation

[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[S:10]([N:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]1[C:19]([OH:21])=O)(=[O:12])=[O:11].C([N:24](CC)CC)C.ClC(OCC)=O.N>O1CCCC1>[NH:3]1[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N:1]=[C:2]1[S:10]([N:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]1[C:19]([NH2:24])=[O:21])(=[O:11])=[O:12]

Participants

Conditions

Temperature: -20 °C

Procedure

1-(1H-Benzo[d]imidazol-2-ylsulfonyl)-2-piperidinecarboxylic acid (17.5 g) [see Preparation 16] was dissolved in tetrahydrofuran (180 ml) and cooled to −20° C. Triethylamine (10.2 ml) was added to the mixture followed by ethyl chloroformate (5.4 ml). The reaction mixture was stirred for 1 hour at −20° C. and 0.88 aqueous ammonia solution (25 ml) was added. The mixture was then stirred for a further 2 hours at room temperature. The organic solvent was removed under reduced pressure and ethyl acetate added. The organic layer was separated, washed with water, dried over magnesium sulphate and the solvent removed under reduced pressure to afford 1-(1H-benzo[d]imidazol-2-ylsulfonyl)-2-piperidinecarboxamide (14.73 g).

Workup

stirringThe mixture was then stirred for a further 2 hours at room temperature
customThe organic solvent was removed under reduced pressure and ethyl acetate
additionadded
customThe organic layer was separated
washwashed with water
dry with materialdried over magnesium sulphate
customthe solvent removed under reduced pressure

Sources & evidence

ORD record: ord-e011619fff344d58b0bd4504e7c11e76
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06610707B1

Reaction notes

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