Water → 1,3-Propanediamine, N-[2-(3,4-dimethoxyphenyl)ethyl]-N-methyl-

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Reaction Steps

1.5 g (5.6 mmol) 3-[[2-(3,4-Dimethoxyphenyl)ethyl]methylamino]propanamide (D1) in dry tetrahydrofuran were added dropwise to a suspension of 0.64 g (1.7 mmol) lithium aluminium hydride in 20 ml dry diethylether whilst stirring. The mixture was heated under reflux for 2 hours then cooled with a bath of ice water before carefully adding dropwise 0.65 ml water, 0.65 ml 15% aqueous NaOH, then 1.95 ml water. The mixture was dried over MgSO4, concentrated in vacuo and the residue was purified twice by chromatography on basic alumina using methylene chloride/methanol: 95/5 then methylene chloride/methanol/30% aqueous ammonia: 90/10/0.1 to yield 0.86 g (60.8%) of the desired compound.

Provenance & Evidence