Dichloromethane → HCID 23142599, compound

HRID 32193Notes

Reaction equation

HRID 32193 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[C:18]([O:20][CH3:21])[C:17]([N:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)=[CH:16][C:15]=2[CH:28]2[CH2:33][C:32]([CH3:35])([CH3:34])[CH2:31][C:30]([CH3:37])([CH3:36])[CH2:29]2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.ClCCl.C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[CH3:21][O:20][C:18]1[C:17]([N:22]2[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]2)=[CH:16][C:15]([CH:28]2[CH2:29][C:30]([CH3:36])([CH3:37])[CH2:31][C:32]([CH3:35])([CH3:34])[CH2:33]2)=[C:14]([N:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[CH:19]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 597693744-[5-Methoxy-4-piperidin-1-yl-2-(3,3,5,5-tetramethylcyclohexyl)phenyl]piperazine-1-carboxylic acid t-butyl ester

Product 1

HCID 23142599HCID 23142599, compoundYield 79.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of the 4-[5-methoxy-4-piperidin-1-yl-2-(3,3,5,5-tetramethylcyclohexyl)phenyl]piperazine-1-carboxylic acid t-butyl ester (88 mg, 0.17 mmol) produced in Example (72a), trifluoroacetic acid (0.25 mL, 3.2 mmol) and dichloromethane (0.5 mL) was stirred for 1 hour and 10 minutes at room temperature. Saturated aqueous solution of sodium hydrogencarbonate was added to the reaction mixture and extraction was performed with ethyl acetate. The separated organic layer was 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 56 mg of the title compound as a red solid.

Workup

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

Sources & evidence

ORD record
ord-c38738af640045bca633ae06ff55ddaf
Source dataset
uspto-grants-2008_09
Patent number
US07425554B2

Reaction notes

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