2-Bromoethanol → 1-Piperazineethanol, 4-(2-methoxyphenyl)-

HRID 1942420Notes

Reaction equation

HRID 1942420 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.Br[CH2:17][CH2:18][OH:19].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:2][O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH2:15][CH2:14][N:13]([CH2:17][CH2:18][OH:19])[CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 9899402N-(2-Methoxyphenyl)piperazine hydrochloride

Product 1

HCID 111073541-Piperazineethanol, 4-(2-methoxyphenyl)-Yield 95%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2.29 g (10 mmol) 1-(2-methoxy-phenyl)-piperazine hydrochloride, 7.1 mL (100 mmol) 2-bromo-ethanol, 5.52 g (40 mmol) potassium carbonate and 100 mL acetonitrile is stirred at 60° C. overnight. Filtration and concentration in vacuum yields the crude product which is purified via column chromatography over silica gel eluting with dichloromethane/ammonia-saturated methanol 98:2.

Workup

  1. filtrationFiltration and concentration in vacuum

Sources & evidence

ORD record
ord-407f724f46ad4e9caec8fc381a21507b
Source dataset
uspto-grants-2013_03
Patent number
US08389555B2

Reaction notes

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