Triethylamine → Benzamide

Temperature

0 °C

As shown in reaction scheme 83, N,N-dimethyl-1-phenylethane-1,2-diamine represented by Formula 101 (439.1 mg, 2.67 mmol, purchased from Alfa Aesar Co.) and triethylamine (0.75 mL, 5.35 mmol) in THF (10 mL) solution were cooled to 0° C. under a nitrogen atmosphere, then, 3-(trifluoromethyl)benzoic acid chloride represented by Formula 153 (613.17 mg, 2.94 mmol, purchased from TCI Co.) in THF (15 mL) solution was slowly added thereto. After agitating the mixture at the same time for 30 minutes, the mixture was left at room temperature for 18 hours. A precipitate generated during the reaction was removed through filtration. The remaining solution was diluted with chloroform and this diluted solution was washed with a potassium carbonate (K2CO3) solution, followed by separation and drying the same with sodium sulfate (Na2SO4). The obtained vacuum-concentrated mixture was subjected to separation and purification through column chromatography (ethyl acetate/hexane/triethylamine, 2:1:0.1, v/v/v) using silica gel (SiO2), resulting in a benzamide compound represented by Formula 83 as a desired product (VVZ-078; 632.5 mg, 70% yield).

1. additionwas slowly added
2. waitthe mixture was left at room temperature for 18 hours
3. customwas removed through filtration
4. additionThe remaining solution was diluted with chloroform
5. washthis diluted solution was washed with a potassium carbonate (K2CO3) solution
6. customfollowed by separation
7. dry with materialdrying the same with sodium sulfate (Na2SO4)
8. concentrationThe obtained vacuum-concentrated mixture
9. customwas subjected to separation and purification through column chromatography (ethyl acetate/hexane/triethylamine, 2:1:0.1, v/v/v)

ORD record

ord-b0d63b3d91504ab78ab660ba1ef98336

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09359346B2