Water → 1-Acetyl-4-(4-hexyloxyphenyl)piperazine

HRID 351546Notes

Reaction equation

HRID 351546 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].C(=O)(O)[O-].[K+].Br[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].O>CS(C)=O.C(OCC)(=O)C>[C:1]([N:4]1[CH2:5][CH2:6][N:7]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:12][CH:11]=2)[CH2:8][CH2:9]1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 81011-BromohexaneHCID 516893Potassium BicarbonateHCID 7124411-(4-(4-Hydroxyphenyl)piperazin-1-yl)ethanone

Product 1

HCID 227132431-Acetyl-4-(4-hexyloxyphenyl)piperazine

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of 1-acetyl-4-(4-hydroxyphenyl) piperazine (20 g) and potassium bicarbonate (12.55 g) in dimethylsulfoxide (200 ml) was added 1-bromohexane (19.12 ml) and stirred for 24 hours at 80° C. The reaction mixture was added to a mixture of water and ethyl acetate. The organic layer was taken and dried over is magnesium sulfate. The magnesium sulfate was filtered off, and the filtrate was evaporated under reduced pressure to give 1-acetyl-4-(4-hexyloxyphenyl)piperazine (14.5 g).

Workup

  1. customdried
  2. filtrationThe magnesium sulfate was filtered off
  3. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-55960f6b25f8486b9db79f648a9dc4ae
Source dataset
uspto-grants-2004_06
Patent number
US06743776B2

Reaction notes

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