Potassium cyanate → HCID 67577951, compound

Participants

Reaction Steps

Potassium cyanate (44 mg) was added to a stirred solution of 3-benzyl-4-(3-[N-isopropylamino]propoxy)aniline dihydrochloride (222 mg) in water (5 mls). The reaction mixture was stirred for 2 hours and the resulting precipitate collected by filtration. The solid collected was purified by flash column chromatography on silica gel (Merck Art No 9385) using a 90:10:1 (v/v/v) mixture of dichloromethane/ethanol/ammonia (density=0.88 g/cm3) as eluent to give a residue which was dissolved in saturated methanolic hydrogen chloride solution. The solution was evaporated to give a solid which was crystallised from ethanol to give 3-benzyl-4-(3-[N-isopropylamino]propoxy)phenylurea hydrochloride as a white solid (582 mg), m.p. 204.7° C., microanalysis, found: C, 63.6; H, 7.6; N, 10.9%; C20H23N3O. HCl requires: C, 63.6; H, 7.47; N, 11.1%; NMR:([CD3 ]2SO): 1.2(6H,d), 2.05(2H,m), 2.9(2H,t), 3.25(1H,m), 3.85(2H,s), 4.0(2H,t), 5.7(2H,s), 6.82(1H,d), 7.05-7.3(7H,m), 8.4(1H,s), 7.5(2H,s); m/z 342(M+H).

Provenance & Evidence