Dichloromethane → HCID 67582441, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (E)-1-benzyl-4-(2-phenylethenyl)-1,2,3,6-tetrahydropyridine (27 g, 100 mmol) in dichloromethane (400 ml) at 0° C. was added 1-chloroethyl chloroformate (13 ml, 120 mmol) via syringe, keeping the temperature below 5° C. The reaction was stirred at 0° C. for 1 hour and then warmed to room temperature over 2 hours. The solvent was evaporated, methanol (500 ml ) added to the residue, and the reaction refluxed for 90 minutes. The reaction was cooled to room temperature, the solvent evaporated to a slurry and ether (≈200 ml) added. The resultant solid was filtered and dried to give the title compound (17 g, 77%); δH (DMSO-d6) 2.55 (2H, br s, tetrahydropyridinyl CH2), 3.25 (2H, br s, tetrahydropyridinyl CH2), 3.71 (2H, br s, tetrahydropyridinyl CH2), 5.92 (1H, br s, tetrahydropyridinyl 5-CH), 6.62 (1H, d, J 16.3 Hz, ArCH=CHC), 6.97 (1H, d, J 16.3 Hz, ArCH=CHC), 7.25 (1H, d, J 7.3 Hz, 4-H), 7.35 (2H, t, J 7.3 Hz, 3-H, 5-H), 7.52 (2H, d, J 7.3 Hz, 2-H, 6-H), and 9.51 (1H, br s, NH); m/z (ES+) 306 (M+1)+.

Provenance & Evidence