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Methylamine → 3-Benzyloxy-1-methylazetidine

HRID 2198850
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HRID 2198850 반응식
[CH2:1]([O:8][CH:9]([CH2:12]Cl)[CH2:10]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:14][NH2:15].[OH-].[Na+]>>[CH2:1]([O:8][CH:9]1[CH2:12][N:15]([CH3:14])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
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참가 물질

4

반응물 3

HCID 6329MethylamineHCID 14798Sodium HydroxideHCID 5155009Benzene, [[2-chloro-1-(chloromethyl)ethoxy]methyl]-

생성물 1

HCID 205173843-Benzyloxy-1-methylazetidine수율 47%

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온도
90 °C

실험 절차

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:

후처리

  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

출처 및 근거

ORD 기록
ord-38558f7f7b6a46b4ad995d93ba04c988
출처 데이터셋
uspto-grants-1982_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04360464

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