Methyl Isobutyl Ketone → (E)-ethyl 4-[methyl(3-phenyl-2-propenyl)amino]-1-piperidinecarboxylate ethanedioate

HRID 466533

反応式

HRID 466533 の反応式
[CH3:1][NH:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:5][CH2:4]1.Cl[CH2:15][CH:16]=[CH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[C:24](=[O:27])([O-:26])[O-].[Na+].[Na+].CC(C)CC(=O)C>O>[C:9]([OH:11])(=[O:10])[C:24]([OH:26])=[O:27].[CH3:1][N:2]([CH2:15]/[CH:16]=[CH:17]/[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:5][CH2:4]1

参加物

6

反応物 4

HCID 7909Methyl Isobutyl KetoneHCID 10340Sodium CarbonateHCID 94242Benzene, (3-chloro-1-propenyl)-HCID 110631401-Piperidinecarboxylic acid, 4-(methylamino)-, ethyl ester

生成物 1

HCID 86744664(E)-ethyl 4-[methyl(3-phenyl-2-propenyl)amino]-1-piperidinecarboxylate ethanedioate

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

実験手順

A mixture of 14 parts of ethyl 4-(methylamino)-1-piperidinecarboxylate, 13 parts of (3-chloro-1-propenyl)benzene, 26.5 parts of sodium carbonate and 240 parts of 4-methyl-2-pentanone was stirred and refluxed over week-end using a water separator. The reaction mixture was cooled, water was added and the layers were separated. The organic phase was dried, filtered and evaporated. The residue was converted into the ethanedioate salt in 2-propanol and 2-propanone. The salt was filtered off and dried, yielding 23.4 parts of (E)-ethyl 4-[methyl(3-phenyl-2-propenyl)amino]-1-piperidinecarboxylate ethanedioate (1:1); mp. 160.2° C. (intermediate 3).

後処理

  1. temperaturerefluxed over week-end
  2. temperatureThe reaction mixture was cooled
  3. customthe layers were separated
  4. customThe organic phase was dried
  5. filtrationfiltered
  6. customevaporated
  7. filtrationThe salt was filtered off
  8. customdried

出典と根拠

ORDレコード
ord-6a171b240b114221a4d4a08d730c2daf
出典データセット
uspto-grants-1992_10
特許番号
US05157035

関連ノート

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