Hydrochloric Acid → [3-(Ethylamino)-4-methoxyphenyl]dimethylamine

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Reaction Steps

N-(3-dimethylamino-6-methoxyphenyl)acetamide 26 (0.10 gm, 0.48 mmoles) was dissolved in 2 ml THF and stirred under argon at room temperature. Borane-methylsulfide complex (0.6 ml, 2.0M, 1.2 mmoles) was added by syringe. After 10 minutes at ambient temperature, the mixture was heated to reflux for 3 hours. After cooling to room temperature, 0.6 ml water was cautiously added with stirring 0.1 ml conc. HCl. After heating for 1 hour, 5 ml DCM and 0.3 ml 2N NaOH were added sequentially with vigorous stirring. The aqueous portion was extracted with three 30 ml portions of DCM which were combined, dried over MgSO4, filtered, and concentrated by rotary evaporation under reduced pressure to give 95 mg of crude [3-(ethylamino)-4-methoxyphenyl]dimethylamine 27.

Provenance & Evidence