Water → HCID 59364341, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N1-(3-chlorophenyl)propane-1,3-diamine (1 g, 5.4 mmol) in dry CH2Cl2 (10 mL), Et3N (1.65 g, 2.27 mL) was added. The resulting mixture was cooled to 0-5° C., a solution of methyl chloroformate (4.0 g, 43 mmol, 5 eq) in dry CH2Cl2 (5 mL) was added drop wise. After addition, the reaction mixture was stirred for 1-2 h at 0-5° C. Upon completion of the reaction, water (15 mL) was added. The aqueous layer was extracted with CH2Cl2 (3×30 mL). The combined organic layers were washed with 10% citric acid (2×10 mL) and brine, then dried over Na2SO4, filtered and concentrated to the crude product which was purified by preparative HPLC to afford methyl 3-(3-chlorophenylamino)propylcarbamate (1.18 g, yield 98%).

Provenance & Evidence