Methyl iodide → HCID 178482467、化合物

HRID 1620486ノート

反応式

HRID 1620486 の反応式
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:4]=1[CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([CH:12]=O)[CH2:8][CH2:7]1.[CH3:24]C(C)([O-])C.[K+].CI.[Cl-].[NH4+].[CH3:34][NH:35][C:36]1[CH2:40][S:39][C:38](=[O:41])[N:37]=1>O1CCCC1.C(O)C.C(OCC)(=O)C>[F:1][C:2]([F:23])([F:22])[C:3]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:4]=1[CH2:5][N:6]1[CH2:11][CH2:10][C:9](/[CH:24]=[C:40]2/[C:36]([NH:35][CH3:34])=[N:37][C:38](=[O:41])[S:39]/2)([CH3:12])[CH2:8][CH2:7]1

参加物

9

反応物 5

HCID 6328Methyl iodideHCID 25517Ammonium Chloride2 回HCID 23665647Potassium tert-butoxide2 回HCID 866786631-[2,4-Bis(trifluoromethyl)benzyl]piperidine-4-carbaldehydeHCID 178482466HCID 178482466、化合物

生成物 1

HCID 178482467HCID 178482467、化合物収率 16.3%

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒2 回

実験手順

To a solution of 1-[2,4-bis(trifluoromethyl)benzyl]piperidine-4-carbaldehyde (372 mg) in tetrahydrofuran (5 mL) were added potassium tert-butoxide (123 mg) and methyl iodide (0.069 mL) under ice-cooling. The reaction mixture was stirred at room temperature for 1 hr under a nitrogen atmosphere. To the reaction mixture were added saturated aqueous ammonium chloride solution/ethyl acetate, and the organic layer was separated, washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give an oil. The obtained oil and 4-(methylamino)-1,3-thiazol-2(5H)-one (143 mg) were suspended in ethanol (5 mL), and potassium tert-butoxide (123 mg) was added. The reaction mixture was stirred at 80° C. for 3 hr. To the reaction mixture were added saturated aqueous ammonium chloride solution/ethyl acetate at room temperature, and the organic layer was separated, washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) and recrystallized from ethyl acetate/heptane to give the title compound (83 mg).

後処理

  1. temperaturecooling
  2. customthe organic layer was separated
  3. washwashed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)
  7. customto give an oil
  8. stirringThe reaction mixture was stirred at 80° C. for 3 hr
  9. customthe organic layer was separated
  10. washwashed with water and saturated brine
  11. dry with materialdried over anhydrous magnesium sulfate
  12. customthe solvent was evaporated under reduced pressure
  13. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)
  14. customrecrystallized from ethyl acetate/heptane

出典と根拠

ORDレコード
ord-7f35b5c9b0c54b2d8376297dac5edaba
出典データセット
uspto-grants-2014_07
特許番号
US08772277B2

反応ノート

読み込み中…