Water → 2-[4-(3-Acetylaminophenyl)piperidin-1-yl]ethanol

HRID 218044Notes

Reaction equation

HRID 218044 reaction equation
Cl.[C:2]([NH:5][C:6]1[CH:7]=[C:8]([CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[CH:9]=[CH:10][CH:11]=1)(=[O:4])[CH3:3].Br[CH2:19][CH2:20][OH:21].C([O-])([O-])=O.[K+].[K+].O>CN(C)C=O>[C:2]([NH:5][C:6]1[CH:7]=[C:8]([CH:12]2[CH2:13][CH2:14][N:15]([CH2:19][CH2:20][OH:21])[CH2:16][CH2:17]2)[CH:9]=[CH:10][CH:11]=1)(=[O:4])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 68602625HCID 68602625, compound

Product 1

HCID 686025242-[4-(3-Acetylaminophenyl)piperidin-1-yl]ethanolYield 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.0 g (7.8 mmol) of 4-(3-acetylaminophenyl)piperidine hydrochloride was dissolved in 20 ml of N,N-dimethylformamide, and then 1.3 g (10.2 mmol) of 2-bromoethanol and 3.2 g (23.4 mmol) of K2CO3 were added to the resulting solution, followed by treating the mixture at 60° C. for 5 hours. The reaction mixture was combined with 100 ml of water and extracted with ethylacetate (70 ml×5), and then the combined organic layer was dried over anhydrous sodium sulfate, and filtered. The solvent was removed from the filtrate under a reduced pressure, and the resulting residue was refined by silica gel column chromatography (10% methanol/CH2Cl2) to obtain 1.14 g (yield 56%) of the title compound.

Workup

  1. additionby treating the mixture at 60° C. for 5 hours
  2. extractionextracted with ethylacetate (70 ml×5)
  3. dry with materialthe combined organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customThe solvent was removed from the filtrate under a reduced pressure

Sources & evidence

ORD record
ord-d63d66c72cb04495b5f159413387c0d9
Source dataset
uspto-grants-2012_06
Patent number
US08198307B2

Reaction notes

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