Water → Ethyl 4-[4-(4-hexyloxyphenyl)piperazin-1-yl]benzoate

HRID 351548Notes

Reaction equation

HRID 351548 reaction equation
Cl.Cl.[CH2:3]([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)[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C(=O)(O)[O-].[K+].F[C:28]1[CH:38]=[CH:37][C:31]([C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:30][CH:29]=1.O>CS(C)=O.C(OCC)(=O)C>[CH2:3]([O:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH2:21][CH2:20][N:19]([C:28]3[CH:38]=[CH:37][C:31]([C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:30][CH:29]=3)[CH2:18][CH2:17]2)=[CH:12][CH:11]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

7

Reactant 4

HCID 962WaterHCID 67976Benzoic acid, 4-fluoro-, ethyl esterHCID 516893Potassium BicarbonateHCID 227131621-(4-Hexyloxyphenyl)piperazine dihydrochloride

Product 1

HCID 22713156Ethyl 4-[4-(4-hexyloxyphenyl)piperazin-1-yl]benzoate

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

To a suspension of 1-(4-hexyloxyphenyl)piperazine dihydrochloride (0.914 g) and potassium bicarbonate (0.564 g) in dimethylsulfoxide (5 ml) was added ethyl p-fluorobenzoate (0.2 ml) and stirred for 10 hours at 150° 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 ethyl 4-[4-(4-hexyloxyphenyl)piperazin-1-yl]benzoate (0.347 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-20d7321285604218920836b49b28c70c
Source dataset
uspto-grants-2004_06
Patent number
US06743776B2

Reaction notes

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