Water → HCID 54242644, compound

HRID 1419934Notes

Reaction equation

HRID 1419934 reaction equation
[CH3:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][C:7]2([OH:13])[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)=[CH:4][CH:3]=1.Br[CH2:17][CH2:18][OH:19].C([O-])([O-])=O.[K+].[K+].O>CC(=O)CC>[OH:19][CH2:18][CH2:17][N:10]1[CH2:9][CH2:8][C:7]([CH2:6][C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:15][CH:14]=2)([OH:13])[CH2:12][CH2:11]1

Participants

6

Reactant 4

HCID 962WaterHCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 105362424-(4-Methylbenzyl)-piperidin-4-ol

Product 1

HCID 54242644HCID 54242644, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture containing 4-(4-methyl-benzyl)-piperidin-4-ol (5.1 g, 25 mmol), 2-bromoethanol (1.8 ml, 25 mmol) and K2CO3 (5.2 g, 37.5 mmol) in 2-butanone (120 ml) was refluxed for 22 hours. H2O (30 ml) was added and the aqueous phase was extracted with ethylacetate. Combined organic phases were dried over Na2SO4, and concentrated. The residue was chromatographed over silica gel (CH2Cl2 --MeOH, 9:1 +NH4OH (1%)) to provide 1-(2-hydroxy-ethyl)-4-(4-methyl-benzyl)-piperidin-4-ol (4.3 g, 73%) as a yellow oil, MS: m/e=235.3 (M+).

Workup

  1. temperaturewas refluxed for 22 hours
  2. extractionthe aqueous phase was extracted with ethylacetate
  3. dry with materialCombined organic phases were dried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was chromatographed over silica gel (CH2Cl2 --MeOH, 9:1 +NH4OH (1%))

Sources & evidence

ORD record
ord-a8e9398e02fe4181bd2c8533d7b06be0
Source dataset
uspto-grants-1999_03
Patent number
US05889026

Reaction notes

Loading…