Methyl Isocyanate → 1-{3-[4-(4-Chlorobenzyl)piperazin-1-yl]propyl}-3-methylurea dihydrochloride

Participants

Reaction Steps

A solution of 1-(3-aminopropyl)-4-(4-chlorobenzyl)piperazine (2.68 g; 10 mmole) and methyl isocyanate (0.57 g; 10 mmole) in methylene chloride (10 ml) was stirred at room temperature overnight. The reaction mixture was evaporated under reduced pressure, and the residue was chromatographed on a silica gel column (1"×24") using a methanolammonium hydroxide gradient (3-6%) with methylene chloride as the eluant. The product (1.0 g; 31% yield) was dissolved in methylene chloride/ether (1:1, 20 ml), and the solution was treated with anhydrous hydrogen chloride to precipitate the title compound as colorless crystals, m.p. 193°-207° C. (decomp.).

Provenance & Evidence