Benzyl Bromide → HCID 15136430, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 1H-pyrrol-1-amine (9.2 g, 0.112 mole) and NaHCO3 (15 g, 0.19 mole) in 50 ml dichloromethane (DCM) at 0° C., was added ethyl chloroformate (11.4 ml, 0.12 mole) in fifteen minutes. After stirring at 0° C. for one hour, then at ambient temperature for four hours, the mixture was filtered and the filtrate was washed with water, then dried (saturated NaCl solution, anhydrous MgSO4). After filtering, the solvent was evaporated to give a solid, 17 g (95%), m.p. 60°-61° C., of N-(1H-pyrrol-1-yl) carbamic acid ethyl ester. To a solution of N-(1H-pyrrol-1-yl) carbamic acid ethyl ester (9.0 g, 0.058 mole) in 30 ml tetrahydrofuran (THF) at 5° C., was added potassium t-butoxide (7.8 g, 0.07 mole) and the mixture was stirred at 5° C. for one hour. To this mixture was added benzyl bromide (7.1 ml, 0.06 mole) in ten minutes, and the mixture stirred at 5° C. for one hour, then at ambient temperature for four hours. This mixture was poured into 100 ml ice-water, stirred for five minutes, then extracted with ethyl acetate. The organic layer was washed with water, then dried (saturated NaCl, anhydrous MgSO4). After filtering, the solvent was evaporated to an oil, 14 g (98%) of N-benzyl-N-(1H-pyrrol-1-yl) carbamic acid ethyl ester. To a solution of N-benzyl-N-(1H-pyrrol-1-yl) carbamic acid ethyl ester (14 g, 0.058 mole) in 15 ml ethylene glycol was added a solution of NaOH (5 g, 0.12 mole) in 10 ml water. After stirring at 120° C. for seven hours, the mixture was poured into 100 ml of iced-water, stirred for five minutes, then extracted with ethyl acetate. The organic layer was washed with water, then dried (saturated NaCl, anhydrous MgSO4). After filtering, the solvent was evaporated to an oil, which was vacuum distilled to give an oil, 7.4 g (74%) of N-benzyl-1H-pyrrol-1-amine, b.p. 85°-125° C./1 mm; m.p. 39°-41° C.

Provenance & Evidence