2-Aminothiophenol → 1-(4-(Benzo[d]thiazol-2-yl)piperidin-1-yl)ethanone

HRID 1068141Notes

Reaction equation

[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10](O)=O)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[SH:20].[OH-].[NH4+]>O>[S:20]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]=[C:10]1[CH:7]1[CH2:8][CH2:9][N:4]([C:1](=[O:3])[CH3:2])[CH2:5][CH2:6]1

Participants

Conditions

Temperature: 110 °C

Procedure

To a mixture of 1.43 g of 1-acetylpiperidine-4-carboxylic acid and 1.05 g of 2-aminothiophenol was added 5 mL of polyphosphoric acid. After stirring at 110° C. for 18 hours, the reaction was cooled to 40° C. The syrup was poured onto ice and water was added to keep the solution temperature below 10° C. The resulting dark brown solution was basified with ammonium hydroxide. Aqueous phase was extracted with EtOAC (3×). The combined organic phases were washed with brine and dried over anhydrous MgSO4. Concentration under reduced pressure afforded 1.41 g of the title compound as a solid.

Workup

temperaturethe reaction was cooled to 40° C
additionwas added
customthe solution temperature below 10° C
extractionAqueous phase was extracted with EtOAC (3×)
washThe combined organic phases were washed with brine
dry with materialdried over anhydrous MgSO4
concentrationConcentration under reduced pressure

Sources & evidence

ORD record: ord-11f7808cf5be44b49b958007e13e894b
Source dataset: uspto-grants-2001_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06248755B1

Reaction notes

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