Dichloromethane → 1-[4-Pyridin-2-yl-2-(3,3,5,5-tetramethylcyclohexyl)phenyl]piperazine

HRID 2218888Notes

Reaction equation

HRID 2218888 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=3)=[CH:16][C:15]=2[CH:26]2[CH2:31][C:30]([CH3:33])([CH3:32])[CH2:29][C:28]([CH3:35])([CH3:34])[CH2:27]2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.ClCCl.[OH-].[Na+]>O.C(OCC)(=O)C>[N:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[C:17]1[CH:18]=[CH:19][C:14]([N:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[C:15]([CH:26]2[CH2:31][C:30]([CH3:33])([CH3:32])[CH2:29][C:28]([CH3:35])([CH3:34])[CH2:27]2)[CH:16]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 597694274-[4-Pyridin-2-yl-2-(3,3,5,5-tetramethylcyclohexyl)phenyl]piperazine-1-carboxylic acid t-butyl ester

Product 1

HCID 231415711-[4-Pyridin-2-yl-2-(3,3,5,5-tetramethylcyclohexyl)phenyl]piperazineYield 90.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-[4-pyridin-2-yl-2-(3,3,5,5-tetramethylcyclohexyl)phenyl]piperazine-1-carboxylic acid t-butyl ester (42 mg, 0.088 mmol) produced in Example (100a), trifluoroacetic acid (0.1 mL, 1.30 mmol) and dichloromethane (1 mL) was stirred for 17 hours and 50 minutes at room temperature. The reaction mixture was cooled in an ice water bath, and then 5N aqueous solution of sodium hydroxide was added 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 then dried over anhydrous sodium sulfate. The desiccant was filtered off and the filtrate was concentrated under reduced pressure to give 30 mg of a crude product of the title compound as a light yellow oil.

Workup

  1. temperatureThe reaction mixture was cooled in an ice water bath
  2. extractionextraction
  3. washThe separated organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationThe desiccant was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-549e5cc879214af28450165d4187fdbe
Source dataset
uspto-grants-2008_08
Patent number
US07410971B2

Reaction notes

Loading…