Sodium hydride → Tert-butyl 4-(2-chlorophenyl)-4-cyanopiperidine-1-carboxylate

HRID 238289

反応式

HRID 238289 の反応式
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11]#[N:12].[C:13]([O:17][C:18](=[O:26])[N:19]([CH2:23][CH2:24]Cl)[CH2:20][CH2:21]Cl)([CH3:16])([CH3:15])[CH3:14]>CN(C=O)C>[C:13]([O:17][C:18]([N:19]1[CH2:23][CH2:24][C:10]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[Cl:3])([C:11]#[N:12])[CH2:21][CH2:20]1)=[O:26])([CH3:16])([CH3:15])[CH3:14]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 76112(o-Chlorophenyl)acetonitrileHCID 11230235N-BOC-N,N-Bis(2-chloroethyl)amine

生成物 1

HCID 21712251Tert-butyl 4-(2-chlorophenyl)-4-cyanopiperidine-1-carboxylate収率 30.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒3 回

反応条件

温度
75 °C

実験手順

Sodium hydride (60% dispersion in mineral oil, 1.28 g, 45 mmol) was suspended in DMF (20 mL) and cooled in an ice bath under a nitrogen atmosphere. (2-Chloro-phenyl)-acetonitrile (1.77 g, 11.7 mmol) in DMF (5 mL) was added slowly, and the mixture stirred for 2 hours. Bis-(2-chloro-ethyl)-carbamic acid tert-butyl ester (3.3 g, 11.1 mmol) in DMF (5 mL) was then added and the mixture heated to 75° C. for 6 hours. The solvent was removed by evaporation under vacuum and the residue dissolved in ethyl acetate (50 mL), washed with water, then brine, dried over magnesium sulphate, filtered and the solvent removed by evaporation under vacuum. The residue was purified by silica chromatography eluting with a mixture of ethyl acetate and hexane. The fractions containing the desired products were combined and the solvent removed by evaporation to give the title compound as an orange gum (1.1 g). LCMS m/z 321.0 [M+H]+. R.T.=4.76 min (Analytical Method 4).

後処理

  1. temperaturecooled in an ice bath under a nitrogen atmosphere
  2. customThe solvent was removed by evaporation under vacuum
  3. dissolutionthe residue dissolved in ethyl acetate (50 mL)
  4. washwashed with water
  5. dry with materialbrine, dried over magnesium sulphate
  6. filtrationfiltered
  7. customthe solvent removed by evaporation under vacuum
  8. customThe residue was purified by silica chromatography
  9. washeluting with a mixture of ethyl acetate and hexane
  10. additionThe fractions containing the desired products
  11. customthe solvent removed by evaporation

出典と根拠

ORDレコード
ord-6dfa5d3e38844f079e39111db87f1805
出典データセット
uspto-grants-2014_02
特許番号
US08642621B2

関連ノート

読み込み中…