Iodine → 1-[1-(4-Bromophenyl)-1-methyl-ethyl]-piperidine

HRID 1888406

反応式

HRID 1888406 の反応式
[Mg].II.Br[C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][CH:6]=1.[C:12]([C:14]([N:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)(C)[CH3:15])#N.C(=O)([O-])[O-].[K+].[K+]>C(OCC)C.C1COCC1>[Br:11][C:8]1[CH:9]=[CH:10][C:5]([C:14]([N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)([CH3:15])[CH3:12])=[CH:6][CH:7]=1

参加物

8

反応物 5

HCID 807IodineHCID 78041,4-DibromobenzeneHCID 11430Potassium CarbonateHCID 2888822-Methyl-2-piperidin-1-ylpropanenitrileHCID 5462224Magnesium

生成物 1

HCID 582663861-[1-(4-Bromophenyl)-1-methyl-ethyl]-piperidine収率 95%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

In a three necked round bottom flask fitted with a condenser and nitrogen stream, was placed a small quantity of ground glass and magnesium turnings (190 mg, 7.40 mmol). The mixture was stirred for 30 minutes under vacuum then placed under nitrogen and iodine added (one small crystal), followed by the rapid addition of 1,4-dibromobenzene (2.43 g, 10.3 mmol) in 15 ml of anhydrous diethyl ether. The reaction mixture was then heated under reflux for 5 minutes. After this time, a solution of 1-(1-cyano-1-methylethyl)-piperidine (1.0 g, 6.60 mmol) in anhydrous THF was added dropwise resulting in the formation of a white precipitate. The reaction mixture was heated under reflux for 1.5 h, before cooling to ambient temperature. The resultant mixture was treated with saturated aqueous potassium carbonate solution and extracted with DCM. The organic extract was dried over magnesium sulfate and concentrated in vacuo. The crude residue was purified by column chromatography (silica, 12 g column, ISCO, 0-40% ethyl acetate in cyclohexane) to afford the title compound (200 mg, 95%) as a colourless oil. LCMS (Method B): RT=1.99 min, M+H+=282, 284.

後処理

  1. customIn a three necked round bottom flask fitted with a condenser
  2. temperatureThe reaction mixture was then heated
  3. temperatureunder reflux for 5 minutes
  4. customresulting in the formation of a white precipitate
  5. temperatureThe reaction mixture was heated
  6. temperatureunder reflux for 1.5 h
  7. extractionextracted with DCM
  8. extractionThe organic extract
  9. dry with materialwas dried over magnesium sulfate
  10. concentrationconcentrated in vacuo
  11. customThe crude residue was purified by column chromatography (silica, 12 g column, ISCO, 0-40% ethyl acetate in cyclohexane)

出典と根拠

ORDレコード
ord-e4a8c15ef92842328732bcd117187329
出典データセット
uspto-grants-2013_08
特許番号
US08501765B2

関連ノート

読み込み中…