Sodium Hydroxide → 4-Phenylpiperidine-4-methanol

HRID 1182730

反応式

HRID 1182730 の反応式
C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:12]1([C:18]2([C:24](O)=[O:25])[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1.O>[C:12]1([C:18]2([CH2:24][OH:25])[CH2:19][CH2:20][NH:21][CH2:22][CH2:23]2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

参加物

7

反応物 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 27236574-Piperidinecarboxylic acid, 4-phenyl-, 4-methylbenzenesulfonate (1:1)HCID 21226445Aluminium lithium hydride

生成物 1

HCID 778964-Phenylpiperidine-4-methanol収率 64.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒3 回

実験手順

To a solution of 4-phenyl-4-piperidinecarboxylic acid 4-toluene-sulfonate (2.0 g, 5.3 mmol) in dry tetrahydrofuran (10 ml) was added 1 M lithium aluminum hydride solution in tetrahydrofuran at 0° C. The reaction mixture was heated at reflux for 90 min. After cooling to 0° C. water (0.4 ml), 2 M aqueous sodium hydroxide solution (0.6 ml) and water (0.8 ml) were added consecutively. The white suspension was stirred for 10 min and diluted with tetrahydrofuran (40 ml). After addition of anhydrous sodium sulfate (18 g) the suspension was stirred for further 10 min. The precipitate was removed by filtration and the filtrate was concentrated in vacuo to give the crude title compound (0.65 g, 64%) as white solid.

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 90 min
  3. additionwere added consecutively
  4. stirringwas stirred for further 10 min
  5. customThe precipitate was removed by filtration
  6. concentrationthe filtrate was concentrated in vacuo

出典と根拠

ORDレコード
ord-6a2c632153c04a47a086e0b9a3f72446
出典データセット
uspto-grants-2014_03
特許番号
US08664216B2

関連ノート

読み込み中…