Triethylamine → 1-(4-(thiazol-2-ylmethyl)-5,6-dihydropyridin-1(2H)-yl)prop-2-en-1-one

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of 2-((1,2,3,6-tetrahydropyridin-4-yl)methyl)thiazole hydrochloride (Intermediate-2) (1.57 g, 5.34 mmol) in anhydrous CH2Cl2 (20 mL) was added triethylamine (4.4 mL, 32.0 mmol), followed by acryloyl chloride (1.3 mL, 16.0 mmol) at 0° C. and the reaction mixture was allowed to stir at 20-35° C. for 16 h. Then the reaction mixture was diluted with water (50 mL) and extracted with ethyl acetate (2×50 mL). The organic layer was washed with brine (50 mL), dried over anhydrous Na2SO4 and filtered. The filtrate was rotary evaporated under vacuum to get residue which was purified by column chromatography using a mixture of 20% ethyl acetate/hexane as an eluent to get the desired compound as a light brown liquid (320 mg, 26%); 1H NMR (400 MHz, DMSO-d6) δ 7.71 (d, J=3.4 Hz, 1H), 7.60 (d, J=2.9 Hz, 1H), 6.88-6.70 (m, 1H), 6.14-6.08 (m, 1H), 5.72-5.60 (m, 2H), 4.12-4.08 (m, 1H), 4.06-3.96 (m, 1H), 3.74-3.70 (m, 2H), 3.66-3.54 (m, 2H), 2.12-2.02 (m, 2H); ES-MS: 235.1 (M+1)+.

Provenance & Evidence