Sodium sulfate decahydrate → 1-Methyl-2-{2-[2-(4-phenylbutyl)phenoxy]ethyl}piperidine

HRID 743239ノート

反応式

HRID 743239 の反応式
C(O[C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23][CH2:24][CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=O)(C)(C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+].[H-]>O1CCCC1>[CH3:6][N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23][CH2:24][CH2:25][CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

参加物

6

反応物 4

HCID 62649Sodium sulfate decahydrateHCID 166653HydrideHCID 108367361-t-Butoxycarbonyl-2-{2-[2-(4-phenylbutyl)phenoxy]ethyl}piperidineHCID 21226445Aluminium lithium hydride

生成物 1

HCID 105723171-Methyl-2-{2-[2-(4-phenylbutyl)phenoxy]ethyl}piperidine収率 69.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of 820 mg of 1-t-butoxycarbonyl-2-{2-[2-(4-phenylbutyl)phenoxy]ethyl}piperidine [prepared as described in Example 31(a)] in 4 ml of tetrahydrofuran was added dropwise to a dispersion of 140 mg of lithium aluminum hydride in 4 ml of tetrahydrofuran, whilst ice-cooling. After the addition was complete, the reaction mixture was heated under reflux for 2 hours and then cooled. Sodium sulfate decahydrate was carefully added to the mixture in order to decompose any excess of the hydride. Insoluble materials were then filtered off, and the filtrate was concentrated by evaporation under reduced pressure. The resulting oily residue was purified by column chromatography through silica gel, using a 20:1 by volume mixture of methylene chloride and methanol as the eluent, to give 455 mg (yield 69%) of the title compound as a colorless oil.

後処理

  1. temperaturecooling
  2. additionAfter the addition
  3. temperaturethe reaction mixture was heated
  4. temperatureunder reflux for 2 hours
  5. temperaturecooled
  6. filtrationInsoluble materials were then filtered off
  7. concentrationthe filtrate was concentrated by evaporation under reduced pressure
  8. customThe resulting oily residue was purified by column chromatography through silica gel
  9. additionby volume mixture of methylene chloride and methanol as the eluent

出典と根拠

ORDレコード
ord-e707e52241a54bed985a44af6ea92504
出典データセット
uspto-grants-1996_09
特許番号
US05556864

反応ノート

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