Dichloromethane → 1-[2-(4,4-Diethylcyclohexyl)phenyl]piperazine

HRID 32210Notes

Reaction equation

HRID 32210 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH:20]2[CH2:25][CH2:24][C:23]([CH2:28][CH3:29])([CH2:26][CH3:27])[CH2:22][CH2:21]2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.ClCCl.C(=O)([O-])[O-].[K+].[K+]>O.C(OCC)(=O)C>[CH2:28]([C:23]1([CH2:26][CH3:27])[CH2:24][CH2:25][CH:20]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[CH2:21][CH2:22]1)[CH3:29]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 59769430HCID 59769430, compound

Product 1

HCID 231417911-[2-(4,4-Diethylcyclohexyl)phenyl]piperazineYield 108.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 4-[2-(4,4-diethylcyclohexyl)phenyl]piperazine-1-carboxylic acid t-butyl ester (1.12 g, 2.80 mmol) produced in Example (38b), trifluoroacetic acid (10 mL, 130 mmol) and dichloromethane (10 mL) was stirred for 10 minutes at an external temperature of 0° C., and the temperature was raised to room temperature followed by stirring for 30 minutes. Potassium carbonate was then gradually added to the reaction mixture to make the mixture basic. Then, ethyl acetate and water were added and extraction was performed with ethyl acetate. The separated organic layer was washed with brine and dried over anhydrous magnesium sulfate. The desiccant was filtered off and then the filtrate was concentrated under reduced pressure. The resultant residue was purified by silica gel column chromatography (dichloromethane/methanol) to give 912 mg of the title compound as a white solid.

Workup

  1. temperaturethe temperature was raised to room temperature
  2. stirringby stirring for 30 minutes
  3. extractionextraction
  4. washThe separated organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationThe desiccant was filtered off
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe resultant residue was purified by silica gel column chromatography (dichloromethane/methanol)

Sources & evidence

ORD record
ord-1c6907e8f5fa4d038bd5bc0eeab7284a
Source dataset
uspto-grants-2008_09
Patent number
US07425554B2

Reaction notes

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