2-Aminothiophenol → 1-(2-Benzothiazol-2-ylmethylpiperidin-1-yl)-2,2,2-trifluoroethanone

HRID 2377995Notes

Reaction equation

C(O[C:4](=O)[CH2:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][N:7]1[C:12](=[O:17])[C:13]([F:16])([F:15])[F:14])C.[NH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[SH:26]>O>[S:26]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[N:19]=[C:4]1[CH2:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][N:7]1[C:12](=[O:17])[C:13]([F:14])([F:15])[F:16]

Participants

Conditions

Temperature: 90 °C

Procedure

[1-(2,2,2-Trifluoroethanoyl)piperidin-2-yl] acetic acid ethyl ester, D28 (1.34 g) and 2-aminothiophenol (1.50 g) were suspended in polyphosphoric acid (30 ml) and heated to 90° C. for 2 h with vigorous stirring. After cooling, the reaction mixture was poured into iced water and stirred vigorously for 1 h. The aqueous solution was then extracted several times with ethyl acetate. After drying (MgSO4), the solvent was removed in vacuo and the residue chromatographed (silica gel) to afford the title compound as an oil (1.2 g).

Workup

temperatureAfter cooling
extractionThe aqueous solution was then extracted several times with ethyl acetate
dry with materialAfter drying (MgSO4)
customthe solvent was removed in vacuo
customthe residue chromatographed (silica gel)

Sources & evidence

ORD record: ord-fe0a6c6294504a7884ec0b76fec06e72
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07470710B2

Reaction notes

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