4-(Trifluoromethoxy)aniline → 2-(4-Trifluoromethoxy-phenyl)-2,8-diaza-spiro[4.5]decane-1,7-dione

HRID 420650

반응식

HRID 420650 반응식
C(O[C:4]([C:6]1([CH2:13][CH2:14]OC)[CH2:11][CH2:10][NH:9][C:8](=[O:12])[CH2:7]1)=[O:5])C.[F:17][C:18]([F:28])([F:27])[O:19][C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=1.[Cl-].C[Al+]C>C1(C)C=CC=CC=1.CCCCCC.CCOC(C)=O>[F:17][C:18]([F:27])([F:28])[O:19][C:20]1[CH:21]=[CH:22][C:23]([N:24]2[CH2:14][CH2:13][C:6]3([CH2:11][CH2:10][NH:9][C:8](=[O:12])[CH2:7]3)[C:4]2=[O:5])=[CH:25][CH:26]=1

참가 물질

7

반응물 3

HCID 6008484-(Trifluoromethoxy)anilineHCID 16686359Dimethylalumanylium chlorideHCID 584784144-(2-Methoxy-ethyl)-2-oxo-piperidine-4-carboxylic acid ethyl ester

생성물 1

HCID 584784112-(4-Trifluoromethoxy-phenyl)-2,8-diaza-spiro[4.5]decane-1,7-dione

시약·촉매·용매 3

HCID 1140Toluene용매HCID 8058Hexane용매HCID 8857Ethyl Acetate용매

실험 절차

4-(2-Methoxy-ethyl)-2-oxo-piperidine-4-carboxylic acid ethyl ester (2 g) and 4-(trifluormethoxy)aniline (3.09 g) were dissolved in toluene (100 ml) under an argon atmosphere at RT, dimethylaluminium chloride in hexane (1 molar, 39.25 ml) was added and the mixture was refluxed for 8 hours. The reaction mixture was then cooled to RT, diluted with AcOEt, quenched with water (9 ml), dried over MgSO4, filtered and the solvent was evaporated off. The residue was adsorbed on silica gel and purified by flash chromatography on silica gel (acetone/CH2Cl2, gradient from 0 to 40%) to give 2-(4-trifluoromethoxy-phenyl)-2,8-diaza-spiro[4.5]decane-1,7-dione as light brown solid. MS (ESI): 329.1 (MH+).

후처리

  1. temperaturethe mixture was refluxed for 8 hours
  2. customquenched with water (9 ml)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe solvent was evaporated off
  6. custompurified by flash chromatography on silica gel (acetone/CH2Cl2, gradient from 0 to 40%)

출처 및 근거

ORD 기록
ord-716235da5c764bd5911ca7ef5b43de48
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08097634B2

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