Sodium Hydroxide → 1-[3-[2-(4-Chlorophenylsulphonylamino)-ethyl]-phenoxy]-2-aminoethane

Participants

Reaction Steps

To a solution of 21.6 g (58.6 mmol) 3-[2-(4-chlorophenylsulphonylamino)-ethyl]-phenoxyacetamide and 175 ml dimethoxyethane one adds portionwise at 15°-20° C. 31.3 g (0.234 mol) anhydrous aluminium chloride and allows to stir further for 30min. One then adds 8.85 g (0.234 mol) NaBH4 portionwise thereto at 15°-20° C. within 1/2 hr. After 3 hrs. stirring while cooling, 130 ml ice-water are carefully added dropwise thereto, whereby the internal temperature is not to exceed 25° C. While cooling withice, one brings the pH value to 8.5 by addition of conc. NaOH, adds 75 ml ethyl acetate thereto and filters. The precipitate is after-washed with ethyl acetate. After separation of the phases, the aqueous phase is also extracted with ethyl acetate. The organic extracts are dried, concentratedto about 80 ml and mixed with 20 ml HCl-containing ether. After cooling, one filters off with suction and then washes with ethyl acetate. Yield 16.7 g (73% of theory) of hydrochloride with the m.p. 187°-190° C.

Provenance & Evidence