Ammonia → [4-(2-Piperidin-1-ylethoxy)phenyl]methanol

HRID 1949989Notes

Reaction equation

HRID 1949989 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10](=O)[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][N:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)=[CH:13][CH:12]=1)C.N>O1CCCC1>[N:20]1([CH2:19][CH2:18][O:17][C:14]2[CH:13]=[CH:12][C:11]([CH2:10][OH:9])=[CH:16][CH:15]=2)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 9838504Ethyl 4-(2-Piperidinoethoxy)benzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 9816107[4-(2-Piperidin-1-ylethoxy)phenyl]methanolYield 82.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of lithium aluminum hydride (1.5 g) in tetrahydrofuran (50 ml) under a nitrogen atmosphere was added 4-(2-piperidin-1-ylethoxy)benzoic acid ethyl ester (5.0 g) on an ice bath, and the solution was refluxed for 1 hour. Ammonia solution was added thereto on an ice bath, the solution was filtered through celite pad, then the solvent was evaporated in vacuo, and [4-(2-piperidin-1-ylethoxy)phenyl]methanol (3.5 g) was obtained. To a solution of this compound (1.7 g) in chloroform (30 ml) was added manganese(IV) oxide (7.5 g), the solution was stirred overnight at room temperature, then filtered, and the solvent was evaporated in vacuo to provide the title compound (1.7 g).

Workup

  1. temperaturethe solution was refluxed for 1 hour
  2. filtrationon an ice bath, the solution was filtered through celite pad
  3. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-4d157906c12144d09ebd4467d0a2d5e7
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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