Benzyl Chloride → 7-Benzyl-2-methyl-2,7-diazaspiro[4.4]nonane-1,3,8-trione

HRID 364050노트

반응식

HRID 364050 반응식
[CH3:1][N:2]1[C:6](=[O:7])[CH2:5][C:4]2([CH2:11][C:10](=[O:12])[NH:9][CH2:8]2)[C:3]1=[O:13].[H-].[Na+].[CH2:16](Cl)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C)C=O>[CH3:1][N:2]1[C:6](=[O:7])[CH2:5][C:4]2([CH2:11][C:10](=[O:12])[N:9]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:8]2)[C:3]1=[O:13]

참가 물질

5

반응물 3

HCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 42826302-Methyl-2,7-diazaspiro[4.4]nonane-1,3,8-trione

생성물 1

HCID 28689347-Benzyl-2-methyl-2,7-diazaspiro[4.4]nonane-1,3,8-trione수율 63.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 1.82 g (10 mmol) 2-methyl-2,7diazaspiro[4.4]nonane-1,3,8-trione in 20 ml N,N-dimethylformamide was added gradually under a nitrogen atmosphere to 0.050 g (10.4 mmol) of 50% oil suspension of sodium hydride which had been previously washed twice with toluene and covered with 10 ml N,N-dimethylformamide. After stirring one hour there was added 1.40 g (11 mmol) of benzyl chloride and stirring was continued overnight at room temperature. After concentrating to a small volume in vacuo, the residue was diluted with 40 ml water and extracted twice with dichloromethane. The combined organic phase was washed with water, dried over magnesium sulfate, and evaporated to give a solid. Crystallization from toluene-hexane afforded 1.74 g of 2-methyl-7-(phenylmethyl)-2,7-diazaspiro[4.4]nonane-1,3,8-trione, mp 157°-158° C. 2-Methyl-7-(phenylmethyl)-2,7-diazaspiro[4.4]nonane Dihydrochloride

후처리

  1. washhad been previously washed twice with toluene
  2. stirringstirring
  3. waitwas continued overnight at room temperature
  4. concentrationAfter concentrating to a small volume in vacuo
  5. additionthe residue was diluted with 40 ml water
  6. extractionextracted twice with dichloromethane
  7. washThe combined organic phase was washed with water
  8. dry with materialdried over magnesium sulfate
  9. customevaporated
  10. customto give a solid
  11. customCrystallization from toluene-hexane

출처 및 근거

ORD 기록
ord-b56693c9690049f4aba464fde88bbd57
출처 데이터셋
uspto-grants-1986_08
특허 번호
US04604401

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