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

HRID 420650

反応式

HRID 420650 の反応式
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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 1140Toluene溶媒HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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+).

後処理

  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%)

出典と根拠

ORDレコード
ord-716235da5c764bd5911ca7ef5b43de48
出典データセット
uspto-grants-2012_01
特許番号
US08097634B2

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