Triethylamine → [3,5-Bis(trifluoromethyl)phenyl][3-(3,4-dichlorophenyl)piperazin-1-yl]methanone

To a cooled solution of CH2Cl2 (103 mL) containing 2-(3,4-dichlorophenyl)piperazine (1.15 g 5.0 mmol), 3,5-bis-(trifluoromethyl)benzoic acid (1.34 g, 5.09 mmol), and N-hydroxybenzotriazole monohydrate (0.688 g, 5.09 mmol) at -20° C. were added Et3N (0.711 mL 5.09 mmol) and N,N-dimethylaminopropyl-ethylcarbodimide (DEC) (0.967 g, 5.09 mmol) under nitrogen. The reaction was kept at -20° C. for an hour and gradually warmed to RT overnight. After stirring 20 h, the reaction was complete and CH2Cl2 (200 mL) was added. The organic solution was washed with 5% NaHCO3 (80 mL) and brine (80 mL, 2×), dried over MgSO4, filtered and concentrated under vacuum to give 2.1 g of crude product. The product was purified by flash chromatography on flash grade silica gel (120 g), eluting with 2% NH3 -MeOH/CH2Cl2 to give a foam solid (1.25 g, 2.65 mmol, 53%). m.p. 50°-53° C.; FAB MS [M+1]+ 470.9;

1. waitThe reaction was kept at -20° C. for an hour
2. washThe organic solution was washed with 5% NaHCO3 (80 mL) and brine (80 mL, 2×)
3. dry with materialdried over MgSO4
4. filtrationfiltered
5. concentrationconcentrated under vacuum
6. customto give 2.1 g of crude product
7. customThe product was purified by flash chromatography on flash grade silica gel (120 g)
8. washeluting with 2% NH3 -MeOH/CH2Cl2

ORDレコード

ord-270b00f8d32a4ffc8d7cede32de8f96b

出典データセット

uspto-grants-1999_04

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05892039