Ammonia → 1H-benzo[d]imidazol-2-ylsulfonyl-2-piperidinecarboxamide
Reaktionsgleichung
[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]Komponenten
6
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- -20 °C
Versuchsvorschrift
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).
Aufarbeitung
- 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
Quellen und Nachweise
- ORD-Eintrag
- ord-e011619fff344d58b0bd4504e7c11e76
- Quelldatensatz
- uspto-grants-2003_08
- Patentnummer
- US06610707B1
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