Hydrochloric Acid → HCID 11701588, compound

Participants

Reaction Conditions

Reaction Steps

3-Chloro-4-methylaniline (10.0 g, 70.6 mmol), 1-bromo-3-chloropropane (34.7 mL, 55.6 g, 353 mmol) and triethylamine (21.4 g, 212 mmol) were charged. The mixture was stirred at 25-28° C. for 24 hrs. Water (50 mL) and methyl ethyl ketone (25 mL) were added for partitioning. The organic layer was washed twice with water (50 mL). Conc. hydrochloric acid (35 mL, 5.7 eq) was dropwise added to the organic layer under ice-cooling. The mixture was stirred at room temperature for 1 hr. The crystals were collected by filtration, washed with diisopropyl ether (10 mL) and dried in vacuo at 50° C. to give the title compound (14.12 g, yield 78.5%) as pale-yellow crystals.

Provenance & Evidence