1-Chloroethyl chloroformate → HCID 22228444, compound

Participants

Reaction Steps

To a solution of the product of step C (550 mg; 1.88 mmol) in toluene (10 mL) was added 1-chloroethyl chloroformate (15 mmol; 1.62 mL) and the reaction was heated to reflux for 36 h. The volatiles were removed in vacuo, the crude carbamate was then dissolved in methanol (10 mL) and the resultant solution was heated to reflux for 2 h. The volatiles were removed in vacuo, the crude amine was dissolved in methylene chloride (100 mL) and the solution was washed with a saturated solution of sodium bicarbonate, brine and the compound dried (Na2SO4). The drying agent was removed by filtration and the volatiles were removed in vacuo to furnish the crude product which was purified on silica gel using a gradient elution (95:5 then 90:10 methylene chloride/methanol (containing 10% v/v ammonium hydroxide) to afford the title compound.

Provenance & Evidence