Hydrochloric Acid → HCID 19974708, compound

Participants

Reaction Steps

A suspension of the above propanamide (19.9 g, 92 mmol) in THF (200 ml) was cooled on an icebath. A 1M solution of borane in THF (100 ml, 100 mmol) was added and the mixture stirred at room temperature for 16 h. Methanol (50 ml) was carefully added followed by 1N hydrochloric acid (50 ml). The volume was concentrated in vacuo to 50 ml, water (200 ml) was added and pH in the aqueous phase was adjusted to 10 with 2N sodium hydroxide. The mixture was extracted with dichloromethane (3×100 ml) and the combined organic phases were extracted with 4N hydrochloric acid. The phases were separated, pH in the aqueous phase was adjusted to 10 with 6N sodium hydroxide and extracted with dichloromethane (2×100 ml). The organic phase was washed with water (50 ml) and dried (MgSO4). The solvent was evaporated in vacuo to give 15.0 g of N-(2-chloro-4-fluorophenyl)-N-(2-methyl-1-propyl)amine.

Provenance & Evidence