Methylamine → 1-Benzyloxy-4-(3-methylaminopropoxy)benzene

Participants

Reaction Steps

To 150 ml of ethanol containing methylamine (16 g) was added 1-benzyloxy-4-(3-bromopropyloxy)benzene (14 g). The solution was heated for 12 hours at 100° under nitrogen at 1000 psi. The solvent was evaporated in vacuo and the residue treated with 20% sodium hydroxide to ~pH10. The oil was extracted with ethyl acetate and converted in its hydrochloride salt in the usual manner to give 8.4 g (70%) of 1-benzyloxy-4-(3-methylaminopropoxy)benzene as its hydrochloride salt, mp 202°-204.

Provenance & Evidence