Methyl 3-(piperidin-1-ylmethyl)benzoate → (3-((Piperidin-1-yl)methyl)phenyl)methanol

HRID 35038Notes

Reaction equation

HRID 35038 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=2)[C:11](OC)=[O:12])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH2:11][OH:12])[CH:15]=[CH:16][CH:17]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 7162043Methyl 3-(piperidin-1-ylmethyl)benzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 7164645(3-((Piperidin-1-yl)methyl)phenyl)methanolYield 71.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-(1-piperidinylmethyl)benzoic acid, methyl ester (17.56 g) and lithium aluminium hydride (2.58 g) in tetrahydrofuran (500 ml) was stirred at room temperature for 30 h and quenched with water. The solid was removed by filtration and the filtrate distilled to give the title compound as a colourless oil (11.1 g) b.p. 135° (10-1 mm). TLC silica; ether; Rf 0.2.

Workup

  1. customquenched with water
  2. customThe solid was removed by filtration
  3. distillationthe filtrate distilled

Sources & evidence

ORD record
ord-c30e1ee979814cb992c1dcd0652bc0cf
Source dataset
uspto-grants-1988_08
Patent number
US04764612

Reaction notes

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