Acetyl chloride → HCID 22628953, compound

Participants

Reaction Conditions

Reaction Steps

1.6 cm3 of triethylamine are added, at room temperature under an argon atmosphere, to a solution of 2 g of N-{1-[bis(4-chlorophenyl)methyl]azetidin-3-yl}-N-(3,5-difluorobenzyl)amine in 75 cm3 of dichloro-methane. The mixture is cooled to around 0° C. before adding dropwise thereto 0.66 cm3 of acetyl chloride, and then it is stirred at room temperature for 16 hours. The reaction mixture is diluted with 50 cm3 of dichloromethane and is then washed with twice 20 cm3 of distilled water. The organic phase is dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure (2.7 kPa). The residue obtained is purified by flash chromatography on silica gel [eluent:dichloromethane/methanol (98/2 by volume)]. 1.2 g of N-{1-[bis(4-chlorophenyl)methyl]azetidin-3-yl}-N-(3,5-difluorobenzyl)acetamide are obtained in the form of a colorless oil [1H NMR spectrum (300 MHz, CDCl3, δ in ppm). A mixture of rotamers is observed. *2.06 and 2.14 (2s:3H in total); 2.97 (mt:2H); 3.43 (mt:2H); 4.20 and 4.25 (2s:1H in total); 4.54 and from 4.75 to 4.80 (mt:1H in total); 4.68 and 4.78 (broad 2s:2H in total); 6.70 (mt:3H); 7.24 (broad s :8H)].

Provenance & Evidence