Sodium Hydroxide → 4-Phenylpiperidine-4-methanol

HRID 1182730

반응식

HRID 1182730 반응식
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

참가 물질

7

반응물 4

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

생성물 1

HCID 778964-Phenylpiperidine-4-methanol수율 64.1%

시약·촉매·용매 2

HCID 962Water용매2회HCID 8028Tetrahydrofuran용매3회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6a2c632153c04a47a086e0b9a3f72446
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08664216B2

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