Water → 4-[4-(4-Octyloxyphenyl)piperazin-1-yl]benzonitrile

HRID 1872358Notes

Reaction equation

HRID 1872358 reaction equation
[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C(=O)([O-])[O-].[K+].[K+].F[C:29]1[CH:36]=[CH:35][C:32]([C:33]#[N:34])=[CH:31][CH:30]=1.O>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([O:9][C:10]1[CH:11]=[CH:12][C:13]([N:16]2[CH2:21][CH2:20][N:19]([C:29]3[CH:36]=[CH:35][C:32]([C:33]#[N:34])=[CH:31][CH:30]=3)[CH2:18][CH2:17]2)=[CH:14][CH:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 145174-FluorobenzonitrileHCID 211823481-(4-(Octyloxy)phenyl)piperazine

Product 1

HCID 211822454-[4-(4-Octyloxyphenyl)piperazin-1-yl]benzonitrileYield 82.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
160 °C

Procedure

To a suspension of 1-(4-n-Octyloxyphenyl)piperazine (1 g)and potassium carbonate (0.476 g) in N,N-dimethylformamide (1 ml) was added p-fluorobenzonitrile (0.347 g), and stirred for 5 hours at 160° 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 4-[4-(4-n-Octyloxyphenyl)piperazine-1-yl]benzonitrile (0.93 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-683a62ed043d432fa938009c8f82d4da
Source dataset
uspto-grants-2000_08
Patent number
US06107458

Reaction notes

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