Methylamine → 3-Benzyloxy-1-methylazetidine

Temperature

90 °C

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 2 N-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 2 N-HCl aqueous solution and further extracted with 50 parts of 2 N-HCl aqueous solution. The water layers were combined, washed with 50 parts of ether and made sufficiently alkaline with 2 N-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 soduim 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:

1. temperatureThe reaction mixture was cooled
2. temperatureThen the mixture was heated
3. distillationto distill off excessive monomethylamine
4. extractionThe remaining liquor was extracted twice with 200 parts of ether
5. washthe extract was washed with 100 parts of water
6. extractionextracted with 100 parts of 2 N-HCl aqueous solution
7. extractionfurther extracted with 50 parts of 2 N-HCl aqueous solution
8. washwashed with 50 parts of ether
9. extractionThe liquor was extracted twice with 100 parts of ether
10. extractionthe ether extract
11. washwas washed in 50 parts of water
12. dry with materialdried over anhydrous soduim sulfate
13. distillationThe solvent was distilled off
14. distillationthe residue was subjected to distillation

ORD record

ord-38558f7f7b6a46b4ad995d93ba04c988

Source dataset

uspto-grants-1982_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04360464