Water → HCID 20074092, compound

HRID 704377Notes

Reaction equation

HRID 704377 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH2:12]([O:14][C:15]([N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)=[O:16])[CH3:13].C(=O)([O-])[O-].[K+].[K+].O>CC(=O)CC>[CH2:12]([O:14][C:15]([N:17]1[CH2:18][CH2:19][N:20]([CH2:2][CH2:3][CH2:4][CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:21][CH2:22]1)=[O:16])[CH3:13]

Participants

6

Reactant 4

HCID 962WaterHCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 11430Potassium CarbonateHCID 2596681-Bromo-4-phenylbutane

Product 1

HCID 20074092HCID 20074092, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent2×

Conditions

Temperature
80 °C

Procedure

A solution of 2.47 g of 1-bromo-4-phenylbutane in 5 ml of 2-butanone was added to a mixture of 1.93 g of 1-ethoxycarbonylpiperazine, 1.76 g of potassium carbonate and 15 ml of 2-butanone at room temperature. After stirring at 80° C. for 12 hours, the mixture was cooled and, after addition of water, extracted with ethyl acetate. The extract was washed with water and saturated aqueous solution of sodium chloride in that order and dried over anhydrous sodium sulfate. The residue obtained after concentration under reduced pressure was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=4:1) to give 1-ethoxycarbonyl-4-(4-phenylbutyl)piperazine. The compound obtained was dissolved in 20 ml of ethanol and 20 ml of 10% aqueous solution of sodium hydroxide, and the solution was stirred at 100° C. for 12 hours. After cooling, the reaction mixture was extracted with ethyl acetate, and the extract was washed with saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. After concentration under reduced pressure, the residue was purified by silica gel column chromatography (eluent:chloroform-methanol-25% aqueous ammonia=100:10:1) to give 1.5 g cf 1-(4-phenylbutyl)piperazine as an oil.

Workup

  1. temperaturethe mixture was cooled
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water and saturated aqueous solution of sodium chloride in that order
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe residue obtained
  6. concentrationafter concentration under reduced pressure
  7. customwas purified by silica gel column chromatography (eluent:hexane-ethyl acetate=4:1)

Sources & evidence

ORD record
ord-dd4da86f11634ff58705cae9a0c17266
Source dataset
uspto-grants-1991_01
Patent number
US04987132

Reaction notes

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