HCID 22506811, compound → 1-[Bis(4-chlorophenyl)methyl]-3-[(3-methylaminophenyl)(methylsulfonyl)methylene]azetidine

Participants

Reaction Steps

2.7 g of 1-[bis(4-chlorophenyl)methyl]-3-{[3-(N-tertbutyloxycarbonyl-N-methylamino)phenyl](methylsulfonyl)methylene}azetidine in 30 cm3 of dioxane and 30 cm3 of a 4.7 N solution of hydrochloric dioxane are stirred for 20 hours. The reaction medium is evaporated to dryness under reduced pressure (2.7 kpa), taken up in 50 cm3 of water and 50 cm3 of ethyl acetate, stirred and neutralized carefully with a saturated aqueous sodium bicarbonate solution. The organic phase is separated, dried over magnesium sulfate, treated with animal charcoal and then concentrated under reduced pressure (2.7 kpa) to a volume of about 25 cm3, then filtered, concentrated to dryness under reduced pressure. 1.3 g of 1-[bis(4-chlorophenyl)methyl]-3-[(3-methylaminophenyl)(methylsulfonyl)methylene]azetidine are obtained in the form of white crystals melting at 228° C. [NMR spectrum in DMSO-d6, T=300K, δ in ppm (300 MHz): 2.65 (3H, s, J=6 Hz, NCH3), 2.95 (3H, s, SCH3) 3.80 (2H, s, NCH2), 4.20 (2H, s, NCH2), 4.80 (1H, s, NCH), 5.85 (1H, q, J=6 Hz, NH), 6.55 (3H, m, 3 CH arom.), 7.15 (1H, t, J=7 Hz, CH arom.), 7.40 (4H, d, L=7 Hz, 4CH arom.), 7.50 (4H, m, 4CH arom.)].

Provenance & Evidence