Hydrochloric Acid → HCID 15606384, compound

Participants

Reaction Conditions

Reaction Steps

Prepare a solution of 18.0 g potassium tert-butoxide in 53 mL NMP and stir the suspension at 20° C. until a clear solution is obtained. Cool the solution to −20° C. Add to the cooled solution a mixture of 9.3 g (53.4 mmol) N-propyl-1H-indol-1-amine, 7.4 g (53.4 mmol) 4-chloro-3-fluoropyridine and 53 mL NMP while maintaining the internal reaction temperature around −15° C. After the addition is over, the reaction mixture is stirred for ˜30 min at −20° C. The reaction mixture is then added to 100 mL water and 13 mL HCl (37%). Then, add 50 mL n-heptane (2×) and separate the phases. Add to the water phase 10 mL NaOH (32%) and extract the water phase twice with 50 mL n-butyl acetate, wash the combined n-butyl acetate phase with 50 mL water. Add to the resulting n-butyl acetate phase 4.5 mL HCl (37%). Distill the mixture using Dean-Stark trap to remove completely the water. During the distillation a solid precipitates. The suspension is cooled to 5° C. and filtered. After drying at 60–70° C., there remains 10.8 g (3-fluoro-pyridin-4-yl)-(indol-1-yl)-propylamine hydrochloride (75%) as a slightly yellow solid.

Provenance & Evidence