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Sodium Hydroxide → (4-Trifluoromethyl-phenyl)-{4-[1-(4-Methoxy2,3-Dimethyl-phenyl)-ethyl]-piperazin-1-yl}-methanone

HRID 967045
Notes
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Reaction equation

HRID 967045 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[CH3:10])=[C:5]([CH3:17])[C:4]=1[CH3:18].[OH-].[Na+].[F:21][C:22]([F:33])([F:32])[C:23]1[CH:31]=[CH:30][C:26]([C:27](Cl)=[O:28])=[CH:25][CH:24]=1>C1(C)C=CC=CC=1>[F:21][C:22]([F:32])([F:33])[C:23]1[CH:24]=[CH:25][C:26]([C:27]([N:14]2[CH2:13][CH2:12][N:11]([CH:9]([C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[C:4]([CH3:18])[C:5]=3[CH3:17])[CH3:10])[CH2:16][CH2:15]2)=[O:28])=[CH:30][CH:31]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 676074-(Trifluoromethyl)benzoyl chlorideHCID 220219311-[1-(4-Methoxy-2,3-dimethyl-phenyl)-ethyl]-piperazine

Product 1

HCID 10136921(4-Trifluoromethyl-phenyl)-{4-[1-(4-Methoxy2,3-Dimethyl-phenyl)-ethyl]-piperazin-1-yl}-methanone

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1-[1-(4-Methoxy-2,3-dimethyl-phenyl)-ethyl]-piperazine (0.02 g, 0.081 mmole) was dissolved in anhydrous toluene and 1N NaOH (1:1) at room temperature. The 4-trifluoromethyl benzoyl chloride (0.013 ml, 0.081 mmole) was added into the reaction mixture. The reaction mixture was stirred at room temperature for 30 minutes. The mixture was washed with 1N NaOH, extracted with EtOAC. The combined organic layers were dried over MgSO4. After removal organic solvent, the residue was purified by SCX column eluted with MeOH and 10% MeOH (NH3) in dichloromethane. (4-Trifluoromethyl-phenyl)-{4-[1-(4-Methoxy2,3-Dimethyl-phenyl)-ethyl]-piperazin-1-yl}-methanone (compound 10) was obtained as a pale yellow oil (0.010 g 30%). Analysis H1 NMR (400MHz, CDCl3): 7.65 (2H, d), 7.495 (2H, d), 7.19 (1H, d), 6.689 (1H, d), 3.764 (3H, s), 3.682 (1H, q), 3.317 (2H, m), 2.506 (6H, m), 2.266 (3H, s), 2.164 (3H, s) 1.286 (3H, d). MS (LC-MS): Calculated for C23H27F3N2O2 420.47, found 421.26 (M+). XII. {5-[1-4-Methoxy-2,3-dimethyl-phenyl)-ethyl]-(1S,4S)-2,5-diaza-bicyclo[2.2.1]hept-2-yl}-(4-trifluoromethyl-phenyl)-methanone (compound 11)

Workup

  1. customat room temperature
  2. washThe mixture was washed with 1N NaOH
  3. extractionextracted with EtOAC
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. customAfter removal organic solvent
  6. customthe residue was purified by SCX column
  7. washeluted with MeOH and 10% MeOH (NH3) in dichloromethane

Sources & evidence

ORD record
ord-38db3dd5c9b4441da58dd48fe029f78d
Source dataset
uspto-grants-2005_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06953801B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes