Dichloromethane → 1-[2-(3,3,5,5-Tetramethylcyclohexyl)-4-thiazol-2-ylphenyl]piperazine

HRID 32242Notes

Reaction equation

HRID 32242 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[S:21][CH:22]=[CH:23][N:24]=3)=[CH:16][C:15]=2[CH:25]2[CH2:30][C:29]([CH3:32])([CH3:31])[CH2:28][C:27]([CH3:34])([CH3:33])[CH2:26]2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.ClCCl.[OH-].[Na+]>O.C(OCC)(=O)C>[CH3:31][C:29]1([CH3:32])[CH2:28][C:27]([CH3:33])([CH3:34])[CH2:26][CH:25]([C:15]2[CH:16]=[C:17]([C:20]3[S:21][CH:22]=[CH:23][N:24]=3)[CH:18]=[CH:19][C:14]=2[N:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)[CH2:30]1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 597694394-[2-(3,3,5,5-Tetramethylcyclohexyl)-4-thiazol-2-ylphenyl]piperazine-1-carboxylic acid t-butyl ester

Product 1

HCID 231428281-[2-(3,3,5,5-Tetramethylcyclohexyl)-4-thiazol-2-ylphenyl]piperazineYield 101.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-[2-(3,3,5,5-tetramethylcyclohexyl)-4-thiazol-2-ylphenyl]piperazine-1-carboxylic acid t-butyl ester (113 mg, 0.234 mmol) produced in Example (99b), trifluoroacetic acid (0.3 mL, 3.89 mmol) and dichloromethane (2 mL) was stirred for 1 hour 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 thereto to make the mixture basic. Next, ethyl acetate and water were added and extraction was performed with ethyl acetate. The separated organic layer was washed with water and brine and then dried over anhydrous sodium sulfate. The desiccant was filtered off and the filtrate was concentrated under reduced pressure to give 91 mg of a crude product of the title compound as a light yellow solid.

Workup

  1. temperatureThe reaction mixture was cooled in an ice water bath
  2. extractionextraction
  3. washThe separated organic layer was washed with water and 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-d4fe5eaf9bf54f24a3889b529ecd3a03
Source dataset
uspto-grants-2008_09
Patent number
US07425554B2

Reaction notes

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