Water → HCID 22494633, compound

HRID 1816719Notes

Reaction equation

HRID 1816719 reaction equation
F[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[CH3:13][O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([N:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[CH3:13][O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([N:28]2[CH2:33][CH2:32][N:31]([C:2]3[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=3)[CH2:30][CH2:29]2)=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 67976Benzoic acid, 4-fluoro-, ethyl esterHCID 22494620HCID 22494620, compound

Product 1

HCID 22494633HCID 22494633, compoundYield 70.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of ethyl 4-fluorobenzoate (1.90 g) and 1-[4-(6-methoxyhexyloxy)phenyl]piperazine (3.00 g) in dimethylsulfoxide (45 ml) was treated with potassium carbonate (4.25 g), and the mixture was heated at 150° C. for 22 hours. After cooling, water (200 ml) was added to the reaction mixture, and the resulting precipitate was collected by filtration, washed with water and dried under reduced pressure at 50° C. for 7 hours to give ethyl 4-[4-[4-(6-methoxyhexyloxy)phenyl]piperazin-1-yl]benzoate (3.20 g) as an ocher solid.

Workup

  1. temperatureAfter cooling
  2. filtrationthe resulting precipitate was collected by filtration
  3. washwashed with water
  4. customdried under reduced pressure at 50° C. for 7 hours

Sources & evidence

ORD record
ord-97cc17aa3e9544e7912313b9765ddd55
Source dataset
uspto-grants-2005_04
Patent number
US06884868B1

Reaction notes

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