Sodium Hydroxide → 1-butyl-4,4-bis(5-fluoro-3-methyl-1H-indol-2-yl)-N,N-dimethylcyclohexanamine

HRID 1011623노트

반응식

HRID 1011623 반응식
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH3:11].[CH2:12]([C:16]1([N:23]([CH3:25])[CH3:24])[CH2:21][CH2:20][C:19](=O)[CH2:18][CH2:17]1)[CH2:13][CH2:14][CH3:15].F[C:27]([F:33])(F)S(O)(=O)=O.[OH-].[Na+]>ClCCl>[CH2:12]([C:16]1([N:23]([CH3:25])[CH3:24])[CH2:21][CH2:20][C:19]([C:6]2[NH:7][C:8]3[C:4]([C:5]=2[CH3:11])=[CH:3][C:27]([F:33])=[CH:10][CH:9]=3)([C:6]2[NH:7][C:8]3[C:4]([C:5]=2[CH3:11])=[CH:3][C:2]([F:1])=[CH:10][CH:9]=3)[CH2:18][CH2:17]1)[CH2:13][CH2:14][CH3:15]

참가 물질

6

반응물 4

HCID 14798Sodium HydroxideHCID 62406Trifluoromethanesulfonic acidHCID 223515035-Fluoro-3-methyl-1H-indoleHCID 57475098HCID 57475098, 화합물

생성물 1

HCID 445128401-butyl-4,4-bis(5-fluoro-3-methyl-1H-indol-2-yl)-N,N-dimethylcyclohexanamine

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

5-fluoro-3-methyl indole (596 mg, 4 mmol) together with 4-butyl-4-(dimethylamino)-cyclohexanone (788 mg, 4 mmol, synthesis cf. WO2008009415, ketone unit Ket-4) was dissolved in dichloromethane (30 ml) and mixed with trifluoromethane sulphonic acid (400 μl, 4.6 mmol). The batch was stirred for 24 h at RT. For work up the reaction mixture was mixed with 2N NaOH (30 ml) and stirred for 20 min at RT. After separation of the organic phase the aqueous phase was extracted with dichloromethane (3×15 ml). The combined organic extracts were dried over Na2SO4 and then concentrated to low volume. The raw product obtained (1.4 g) was purified by column chromatography [silica gel 60 (50 g); ethyl acetate (500 ml)].

후처리

  1. stirringstirred for 20 min at RT
  2. customAfter separation of the organic phase the aqueous phase
  3. extractionwas extracted with dichloromethane (3×15 ml)
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. concentrationconcentrated to low volume

출처 및 근거

ORD 기록
ord-43ab929d60a9407b913402be9632b63b
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07977370B2

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