1,2-Dichloroethane → HCID 23142194, compound

HRID 32157Notes

Reaction equation

HRID 32157 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[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[CH2:10][CH2:9]1)=O)(C)(C)C.ClCCCl.FC(F)(F)C(O)=O.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.O>[CH:20]1([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][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 59769455HCID 59769455, compound

Product 1

HCID 23142194HCID 23142194, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of the crude product of 4-(2-cyclooctylphenyl)piperazine-1-carboxylic acid t-butyl ester produced in Example (46c), 1,2-dichloroethane (2 mL) and water (0.2 mL) was added trifluoroacetic acid (0.500 mL, 6.490 mmol), followed by stirring for 5 hours and 30 minutes at room temperature. Aqueous solution of potassium carbonate was added to the mixture to make the mixture basic. Ethyl acetate was then added thereto and extraction was performed three times with ethyl acetate. The organic layers were dried over anhydrous sodium sulfate. The desiccant was filtered off and the filtrate was concentrated under reduced pressure. The resultant residue was purified by NH silica gel column chromatography (ethyl acetate/heptane) to give 75 mg of the title compound as a light yellow oil.

Workup

  1. extractionextraction
  2. dry with materialThe organic layers were dried over anhydrous sodium sulfate
  3. filtrationThe desiccant was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe resultant residue was purified by NH silica gel column chromatography (ethyl acetate/heptane)

Sources & evidence

ORD record
ord-e19947f9e58e4841b521ad227cc394ff
Source dataset
uspto-grants-2008_09
Patent number
US07425554B2

Reaction notes

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