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

HRID 967045
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HRID 967045 반응식
[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
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참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-38db3dd5c9b4441da58dd48fe029f78d
출처 데이터셋
uspto-grants-2005_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06953801B2

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