Triethylamine → HCID 22485633, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1,3-bis-(4-chlorophenyl)-propan-2-one (3.20 g, 11.46 mmol), (Yang, H. and Hay, A. S., Synthesis, 1992, 467-472), in anhydrous ethanol (25 ml) was treated successively with titanium (IV) isopropoxide (6.8 ml, 22.9 mmol), methylamine hydrochloride (1.55 g, 22.9 mmol) and triethylamine (3.2 ml, 22.9 mmol). The resulting mixture was stirred at 22° C. for 18 h and then treated with sodium borohydride (0.65 g, 17.2 mmol). After 6 h at 22° C., the reaction mixture was quenched by the addition of 2 N aqueous ammonia (60 ml) and the resulting precipitate was filtered and rinced with ether. The combined ether extracts were washed with brine, dried (anhydrous sodium carbonate) and concentrated. Distillation of the residue in vacuo gave 2.60 g (77% yield) of the title amine as a clear oil: bp 135-140° C./0.2 torr, (bulb to bulb distillation, air bath temperature). 1HNMR 400 MHz (C6D6) δ (ppm): 2.19 (3H, s, NCH3), 2.42 (4H, d, J=6.5 Hz, CH2), 2.69 (1H, m, CH), 6.84 (4H, d, J=8.5 Hz, aromatics), 7.22 (4H, d, J=8.5 Hz, aromatics). The hydrochloride salt was obtained as a white solid. Anal. calcd for C16H17C2N—HCl: C, 58.11; H, 5.49; N, 4.24. Found: C, 57.85; H, 5.35; N, 4.13.

Provenance & Evidence