Hydrochloric Acid → HCID 13279972, compound

Participants

Reaction Steps

1-[1-(4-Methoxyphenyl)cyclobutyl]ethylamine (2.8 g) was heated to 120° C. and 4-pyridinecarboxaldehyde (2.1 g) was added and the mixture was heated at 120°-200° C. for 2 hours. The mixture was allowed to cool and diluted with methanol. Sodium borohydride (1.75 g) was added and the resulting mixture heated under reflux for 21/2 hours. After standing at room temperature for 16 hours the mixture was poured into water, treated with 5N hydrochloric acid and then basified with 5N aqueous sodium hydroxide solution. The product was extracted into ether and the ether extracts were washed with water, dried and evaporated to dryness to give a red oil. The oil was purified by distillation and the distillate dissolved in ether and treated with a solution of excess maleic acid in ether to give a white solid and a sticky yellow gum. Recrystallisation of the white solid from propan-2-ol and ether gave N-(4-pyridylmethyl)-1-[1-(4-methoxyphenyl)cyclobutyl]-ethylamine (1.25) maleate as a pale yellow solid (m.p. 110°-113° C.).

Provenance & Evidence