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

HRID 351531Notes

Reaction equation

HRID 351531 reaction equation
[H-].[Na+].[C:3]([N:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)(=[O:5])[CH3:4].Br[CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.O>CN(C)C=O.C(OCC)(=O)C>[C:3]([N:6]1[CH2:7][CH2:8][N:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)=[CH:14][CH:13]=2)[CH2:10][CH2:11]1)(=[O:5])[CH3:4]

Participants

7

Reactant 4

HCID 962WaterHCID 7960Cyclohexyl bromideHCID 24758Sodium hydrideHCID 7124411-(4-(4-Hydroxyphenyl)piperazin-1-yl)ethanone

Product 1

HCID 227132051-Acetyl-4-(4-cyclohexyloxyphenyl)piperazine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of sodium hydride (60% suspension in mineral oil) (1.18 g) in dimethylformamide (25 ml) was added 1-acetyl-4-(4-hydroxyphenyl)piperazine (5 g) and bromocyclohexane (5.59 ml) and stirred for 1 hour at 100° C. The reaction mixture was added to a mixture of water and ethyl acetate. The organic layer was taken and dried over magnesium sulfate. The magnesium sulfate was filtered off, and the filtrate was evaporated under reduced pressure to give 1-acetyl-4-(4-cyclohexyloxyphenyl)piperazine (0.92 g).

Workup

  1. dry with materialdried over magnesium sulfate
  2. filtrationThe magnesium sulfate was filtered off
  3. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-eb52e27e486347f98cfeb356361f011b
Source dataset
uspto-grants-2004_06
Patent number
US06743776B2

Reaction notes

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