Water → HCID 68160137, compound

HRID 1468771Notes

Reaction equation

HRID 1468771 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]1([C:13]2[CH:18]=[CH:17][C:16]([CH2:19][C:20](OC)=[O:21])=[C:15]([CH3:24])[CH:14]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.O.[OH-].[Na+]>O1CCCC1>[N:7]1([C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][OH:21])=[C:15]([CH3:24])[CH:14]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 86669145HCID 86669145, compound

Product 1

HCID 68160137HCID 68160137, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of lithium aluminum hydride (2.53 g, 66.7 mmol) in tetrahydrofuran (100 ml) was added dropwise methyl (4-piperidin-1-yl-methyl-phenyl)acetate (5.50 g, 22.2 mmol) at 0° C. under nitrogen atmosphere. The mixture was stirred at 0° C. for 2 hours. Water (2.5 ml), 15 wt % aqueous solution of sodium hydroxide (2.5 ml) and water (7.5 ml) was added to the mixture sequentially at 0° C. The mixture was filtrated through a pad of Celite, and concentrated in vacuo. The residue was purified by silica gel column chromatography (eluent; ethyl acetate/methanol=90/10 to 80/20) to afford 2-(4-piperidin-1-yl-methyl-phenyl)ethanol as a colorless oil (4.27 g, 19.5 mmol, 88%).

Workup

  1. filtrationThe mixture was filtrated through a pad of Celite
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by silica gel column chromatography (eluent; ethyl acetate/methanol=90/10 to 80/20)

Sources & evidence

ORD record
ord-d27cafa879c5494a88b790048d10b7dd
Source dataset
uspto-grants-2015_04
Patent number
US09006232B2

Reaction notes

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