Cyclopropanecarbonyl chloride → HCID 18606996, compound

Participants

Reaction Steps

To a solution of 2.0 g of (±)-cis-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-5-[2-(dimethylamino)ethyl]naphtho[1,2-b]-1,4-thiazepin-4(5H)-one in 25 mL pyridine was added dropwise at ice-bath temperature 0.9 g of cyclopropanecarboxylic acid chloride and the solution was kept at this temperature for 17 hours. The mixture was concentrated and the residue, in water, was made basic with concentrated ammonium hydroxide. The aqueous suspension was extracted with ethyl acetate (3×60 mL). The combined ethyl acetate solutions were washed with brine and dried (magnesium sulfate). Removal of the solvent gave 2.3 g (100%) of (±)-cis-3-[(cyclopropylcarbonyl)oxy]-2,3-dihydro-5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)naphtho[1,2-b]-1,4-thiazepin-4(5H)-one as an amorphous compound.

Provenance & Evidence