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

HRID 464974ノート

反応式

HRID 464974 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of 1.82 g (10 mmol) 2-methyl-2,7-diazaspiro[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 to afford 1.74 g of 2-methyl-7-(phenylmethyl)-2,7-diazaspiro[4.4]nonane-1,3,8-trione, mp 157°-158° C.

後処理

  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

出典と根拠

ORDレコード
ord-25620361e832431d9886472192d7bf2c
出典データセット
uspto-grants-1985_10
特許番号
US04550103

反応ノート

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