Methylamine → 3-Benzyloxy-1-methylazetidine

Participants

Reaction Conditions

Reaction Steps

21.9 parts of 2-benzyloxy-1,3-dichloro-propane and 77.5 parts of monomethylamine (40% aqueous solution) were added to an autoclave and they were heated at 90° C. for 48 hours with agitation. The reaction mixture was cooled and 120 parts of 2N-NaOH aqueous solution were added thereto. Then the mixture was heated to distill off excessive monomethylamine. The remaining liquor was extracted twice with 200 parts of ether, and the extract was washed with 100 parts of water, extracted with 100 parts of 2N-HCl aqueous solution and further extracted with 50 parts of 2N-HCl aqueous solution. The water layers were combined, washed with 50 parts of ether and made sufficiently alkaline with 2N-NaOH aqueous solution. The liquor was extracted twice with 100 parts of ether, and the ether extract was washed in 50 parts of water and dried over anhydrous sodium sulfate. The solvent was distilled off and the residue was subjected to distillation to yield 8.3 parts of 3 -benzyloxy-1-methylazetidine boiling at 80° - 82° C. The yield was 47%. The results of infra-red spectrum analysis and nuclear magnetic resonance analysis of the product are as follows:

Provenance & Evidence