Methylamine → HCID 15541820, compound

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Reaction Steps

A mixture of (E)-N-[4-(3-aminophenyl)-3-butenyl]phthalimide (3.50 g, 12.0 mmol) in ethanol (50 mL) was treated with 50 g of a 25% (w/w) solution of methylamine in ethanol. The resulting yellow solution was stirred at room temperature for 3 h and concentrated on a rotary evaporator. The product was vacuum dried at 50° C. for 1 h to give 4.26 g of a viscous, orange-yellow oil. The oil was purified by column chromatography on silica gel (200 g), eluting with methanol-concentrated ammonium hydroxide (10:1, v/v). Based upon TLC analysis, selected fractions were combined and concentrated on a rotary evaporator. The product was purified by vacuum distillation (bulb to bulb) to give 124 mg (6.4%) of a colorless oil, bp 105-110° C. at 0.075 mm Hg. Purification of a second fraction by vacuum distillation produced an additional 141 mg of a colorless oil, bp 104-105° C. at 0.075 mm Hg, bringing the total yield to 249 mg (12.8%).

Provenance & Evidence