Piperidine → 4-Piperidin-1-ylbenzonitrile

HRID 2244280ノート

反応式

HRID 2244280 の反応式
F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[NH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.C(=O)([O-])[O-].[K+].[K+]>CN1CCCC1=O.O>[N:10]1([C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

参加物

6

反応物 3

HCID 8082PiperidineHCID 11430Potassium CarbonateHCID 145174-Fluorobenzonitrile

生成物 1

HCID 7667714-Piperidin-1-ylbenzonitrile収率 92%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
120 °C

実験手順

A mixture of 4-fluorobenzonitrile (1 g, 8.26 mmol), piperidine (0.90 mL, 9.08 mmol) and potassium carbonate (2.28 g, 16.51 mmol) in dry 1-methyl-2-pyrrolidinone (10 mL) was stirred at 120° C. under nitrogen for 20 hours. The cooled reaction mixture was then diluted with water (100 mL) and extracted with ethyl acetate (100 mL). The organic extract was washed with water (100 mL) and brine (100 mL), dried over anhydrous magnesium sulfate, and concentrated in vacuo to afford an orange oil. Purification by flash chromatography using a solvent gradient of 1 to 7% ethyl acetate in hexane gave an orange oil that was crystallized from hexane to afford the title compound (1.41 g, 92%) as an orange crystalline solid, m.p. 54° C.

後処理

  1. customThe cooled reaction mixture
  2. extractionextracted with ethyl acetate (100 mL)
  3. extractionThe organic extract
  4. washwas washed with water (100 mL) and brine (100 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customto afford an orange oil
  8. customPurification by flash chromatography
  9. customgave an orange oil that
  10. customwas crystallized from hexane

出典と根拠

ORDレコード
ord-e42f5c9287e24e549b5f70e9d8945dce
出典データセット
uspto-grants-2010_03
特許番号
US07678787B2

反応ノート

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