Aluminium lithium hydride → (4-(Piperidin-2-yl)phenyl)methanol

HRID 81418Notes

Reaction equation

HRID 81418 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].Cl.[NH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[C:14]1[CH:23]=[CH:22][C:17]([C:18](OC)=[O:19])=[CH:16][CH:15]=1>C1COCC1>[NH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[C:14]1[CH:23]=[CH:22][C:17]([CH2:18][OH:19])=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 44607826Methyl 4-(piperidin-2-yl)benzoate hydrochloride

Product 1

HCID 21985051(4-(Piperidin-2-yl)phenyl)methanolYield 99.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of LiAlH4 (72 mg, 1.8 mmol) in 2 ml of anhydrous THF is added dropwise a solution of methyl 4-(piperidin-2-yl)benzoate hydrochloride (250 mg, 0.98 mmol) in THF at 0° C. The reaction mixture is stirred at room temperature for 4 hours, and is then carefully quenched with water at 0° C. After filtration, the filtrate is evaporated to dryness to give 187 mg of crude product as white solids, which is used for the next reaction without further purification. MS (ESI) m/z 192.1 [M+H]+.

Workup

  1. customis then carefully quenched with water at 0° C
  2. filtrationAfter filtration
  3. customthe filtrate is evaporated to dryness

Sources & evidence

ORD record
ord-eb9554b6207c4e1881f703e71a37fcf6
Source dataset
uspto-grants-2014_09
Patent number
US08846693B2

Reaction notes

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