Tetrahydrofuran → 1-Methyl-4-piperidinemethanol

HRID 1767751Notes

Reaction equation

HRID 1767751 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([CH3:12])[CH2:8][CH2:7]1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.[OH-].[Na+]>CCOCC.O>[CH3:12][N:9]1[CH2:10][CH2:11][CH:6]([CH2:4][OH:3])[CH2:7][CH2:8]1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 11062856Ethyl 1-methylpiperidine-4-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 2719711-Methyl-4-piperidinemethanolYield 68%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

1-Methyl-4-piperdine carboxylic acid ethyl ester (8.95 g, 53 mmol) was dissolved in ether (100 ml) and a 1N solution of lithium aluminium hydride in tetrahydrofuran (57 ml, 57.5 mmol) added at 0° C. and the reaction mixture allowed to warm to ambient temperature and stirred for 3 hours. Water (2 ml), 2N sodium hydroxide (4 ml) and a further portion of water (2 ml) was added and the precipitate collected by suction filtration. The filtrate was evaporated to afford the title compound (4.6 g, 68% yield) as a colourless oil:

Workup

  1. filtrationthe precipitate collected by suction filtration
  2. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-d6721fbbe50a4879af364c52f82c07aa
Source dataset
uspto-grants-2007_06
Patent number
US07235559B1

Reaction notes

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