4-(2-chloroethyl)benzenesulfonamide

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture containing 3-(R,S)-(1-carbamoyl-1,1-diphenylmethyl)pyrrolidine (0.3 g--see Preparation 8), 4-sulphamoylphenethyl chloride (0.23 g--see J. Pharm. Pharmacol., 16, 541, (1964)), sodium bicarbonate (0.4 g) and acetonitrile (10 ml) was heated under reflux for 2 hours. A further portion of sodium bicarbonate (1 g) was added followed by potassium iodide (0.2 g) and the mixture was heated under reflux for 2 hours. On cooling to room temperature, water (60 ml) was added and the mixture was extracted with dichloromethane (3×50 ml). The combined dichloromethane extracts were dried (MgSO4) and concentrated in vacuo to give a glass which was purified by column chromatography on silica eluting with dichloromethane containing methanol (0% up to 10%). The product-containing fractions were combined and concentrated in vacuo to give the title compound as a colourless foam, yield, 0.11 g. was heated under reflux for 2 hours the mixture was heated under reflux for 2 hours the mixture was extracted with dichloromethane (3×50 ml) The combined dichloromethane extracts were dried (MgSO4) concentrated in vacuo to give a glass which was purified by column chromatography on silica eluting with dichloromethane containing methanol (0% up to 10%) concentrated in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 4-(2-chloroethyl)benzenesulphonamide (2.00 g), 1-acetylpiperazine (1.17 g), sodium iodide (1.37 g) and sodium bicarbonate (0.84 g) in n-butanol was heated under reflux with stirring for 66 hours. The mixture was cooled slightly and filtered. The filtrate was allowed to stand and the solid that crystallised out was filtered off and recrystallised from ethyl acetate/methanol to give the title compound (1.10 g), m.p. 203°-204.5° C. was heated under reflux The mixture was cooled slightly filtered the solid that crystallised out was filtered off recrystallised from ethyl acetate/methanol