Water → 2-(4-Methyl-2-phenyl-1-piperazinyl)-3-pyridinemethanol

HRID 843245Notes

Reaction equation

HRID 843245 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[C:13]([C:14](O)=[O:15])=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:4]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>C1COCC1>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[C:13]([CH2:14][OH:15])=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:4]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 98391882-(4-Methyl-2-phenylpiperazin-1-yl)pyridine-3-carboxylic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 102214352-(4-Methyl-2-phenyl-1-piperazinyl)-3-pyridinemethanolYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

In 150 mL of THF was dissolved 10.2 g of 2-(4-methyl-2-phenylpiperazin-1-yl)pyridine-3-carboxylic acid under nitrogen atmosphere. To 300 mL of THF was added 10.2 g of lithium aluminum hydride, and the above THF solution was added in a thin stream to the mixture over 50 minutes under reflux. After refluxing the mixture for 4 hours, the mixture was cooled to 0° to 5° C., and 40.5 mL of water was gradually added in a thin stream thereto. Aluminum hydroxide was separated therefrom by filtration, and the filtrate was concentrated with an evaporator. The residue was allowed to recrystallize from an ether, to give 8.6 g of 2-(4-methyl-2-phenylpiperazin-1-yl)pyridine-3-methanol. Its yield was 98%.

Workup

  1. temperatureunder reflux
  2. temperatureAfter refluxing the mixture for 4 hours
  3. temperaturethe mixture was cooled to 0° to 5° C.
  4. customAluminum hydroxide was separated
  5. filtrationby filtration
  6. concentrationthe filtrate was concentrated with an evaporator
  7. customto recrystallize from an ether

Sources & evidence

ORD record
ord-4937aa2cbb76468caee4de10ae3d2455
Source dataset
uspto-grants-2002_04
Patent number
US06376668B1

Reaction notes

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