Water → 4-(4-Indan-2-yl-piperazin-1-yl)benzoic acid ethyl ester

HRID 1977299

Reaction equation

HRID 1977299 reaction equation
Cl.Cl.[CH2:3]([O:5][C:6](=[O:19])[C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[CH:9][CH:8]=1)[CH3:4].C(=O)(O)[O-].[K+].[CH2:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:27][CH:26]1OS(C)(=O)=O.O>C(#N)C>[CH2:3]([O:5][C:6](=[O:19])[C:7]1[CH:8]=[CH:9][C:10]([N:13]2[CH2:14][CH2:15][N:16]([CH:26]3[CH2:25][C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH2:27]3)[CH2:17][CH2:18]2)=[CH:11][CH:12]=1)[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 2552212,3-Dihydro-1h-inden-2-yl methanesulfonateHCID 516893Potassium BicarbonateHCID 700526324-Piperazin-1-yl-benzoic acid ethyl ester dihydrochloride

Product 1

HCID 700560464-(4-Indan-2-yl-piperazin-1-yl)benzoic acid ethyl esterYield 33.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 4-piperazin-1-yl-benzoic acid ethyl ester dihydrochloride (1 g) and potassium bicarbonate (1.57 g) in acetonitrile (10 ml) was added methanesulfonic acid indane-2-yl ester (0.69 g) and the mixture was stirred under refluxing for 8 hours. The reaction mixture was pulverized with water. The precipitate was collected by filtration and dried over under reduced pressure. The powder was purified by column chromatography on silica gel using methanol/dichloromethane (50:1) as the eluent to give 4-(4-indan-2-yl-piperazin-1-yl)benzoic acid ethyl ester (0.38 g).

Workup

  1. temperatureunder refluxing for 8 hours
  2. filtrationThe precipitate was collected by filtration
  3. customdried over under reduced pressure
  4. customThe powder was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-c7c5d80d58da4ba2bdaa017df586efd2
Source dataset
uspto-grants-2001_05
Patent number
US06232290B1

Linked notes

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