Sodium Hydroxide → 4-Phenylpiperidine-4-methanol

HRID 1182730Notes

Reaction equation

HRID 1182730 reaction equation
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

Participants

7

Reactant 4

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

Product 1

HCID 778964-Phenylpiperidine-4-methanolYield 64.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent3×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-6a2c632153c04a47a086e0b9a3f72446
Source dataset
uspto-grants-2014_03
Patent number
US08664216B2

Reaction notes

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