Water → HCID 19826895, compound

Participants

Reaction Steps

A solution of 3-thienylethyl formamide (62.0 g) in dry diethylether (100 ml) was added dropwise over 1 hour to a stirred suspension of lithium aluminium hydride (19.0 g) in diethylether (500 ml) at room temperature under nitrogen. After 2 hours at reflux temperature the mixture was allowed to cool and the following were added, water (19 ml), 2M sodium hydroxide (38 ml) and water (57 ml). After vigorous stirring for 0.5 hours the suspension was filtered and the filtrate evaporated. The liquid residue (58 g) was dissolved in ethanol (60 ml) and ethanolic hydrogen chloride (~5M, 90 ml) added. After cooling the white crystals of methyl thiophene-3-ethylamine hydrochloride (m.p. 149°) were filtered. The hydrochloride salt was converted to the free base by extraction between dichloromethane and aqueous ammonia, followed by distillation to give methyl thiophene-3-ethylamine (b.p. 78° at 2 mmHg) as a colourless liquid.

Provenance & Evidence