Potassium Carbonate → 2,4-Bis(trifluoromethyl)benzamide

HRID 659187

反応式

HRID 659187 の反応式
N[C@H]1CCCC[C@H]1[NH:8][C:9](=[O:26])[C:10]1[C:15]([C:16]([F:19])([F:18])[F:17])=[CH:14][C:13]([C:20]([F:23])([F:22])[F:21])=[CH:12][C:11]=1OC.C(=O)([O-])[O-].[K+].[K+].[I-].C([N+]1(C)CCC(=O)CC1)C>C(O)C>[F:21][C:20]([F:22])([F:23])[C:13]1[CH:14]=[C:15]([C:16]([F:19])([F:17])[F:18])[C:10]([C:9]([NH2:8])=[O:26])=[CH:11][CH:12]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 110975681-Ethyl-1-methyl-4-oxopiperidin-1-ium iodideHCID 58062915cis-N-(2-Amino-cyclohexyl)-2-methoxy-4,6-bis-trifluoromethyl-benzamide2 回

生成物 1

HCID 27360992,4-Bis(trifluoromethyl)benzamide収率 120%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

cis-N-(2-Amino-cyclohexyl)-2-methoxy-4,6-bis-trifluoromethyl-benzamide (intermediate H) (400 mg, 1.04 mmol) was dissolved in 27 mL ethanol. Potassium carbonate (86 mg, 0.062 mmol) and 1-ethyl-1-methyl-4-oxo-piperidinium iodide (420 mg, 1.56 mmol) were added. The reaction mixture was refluxed for 2 h. The solvent was evaporated off. The residue was extracted with saturated sodium bicarbonate solution and ethyl acetate. The combined organic phases were dried on sodium sulfate, filtered and evaporated. Purification of the residue by flash chromatography on silica gel (dichloromethane/ethyl acetate 1:0→1:1) yielded cis 2-methoxy-N-2-(4-oxo-piperidin-1-yl)-cyclohexyl]-4,6-bis-trifluoromethyl-benzamide as a light yellow solid (321 mg, 66%), MS: m/e=467.2 [(M+H)+].

後処理

  1. temperatureThe reaction mixture was refluxed for 2 h
  2. customThe solvent was evaporated off
  3. extractionThe residue was extracted with saturated sodium bicarbonate solution and ethyl acetate
  4. customThe combined organic phases were dried on sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customPurification of the residue by flash chromatography on silica gel (dichloromethane/ethyl acetate 1:0→1:1)

出典と根拠

ORDレコード
ord-49e60f7aeb9c4e0483ae6fd865722406
出典データセット
uspto-grants-2011_12
特許番号
US08080541B2

関連ノート

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