2-Chloronicotinonitrile → tert-Butyl4-(3-cyano-2-pyridinyl)-1-piperazinecarboxylate

HRID 645667ノート

反応式

HRID 645667 の反応式
Cl[C:2]1[N:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11].C(=O)([O-])O.[K+]>CN(C)C=O>[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][N:20]([C:2]2[C:3]([C:4]#[N:5])=[CH:6][CH:7]=[CH:8][N:9]=2)[CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:11])[CH3:12]

参加物

5

反応物 3

HCID 810792-ChloronicotinonitrileHCID 143452tert-Butyl piperazine-1-carboxylateHCID 516893Potassium Bicarbonate

生成物 1

HCID 22061422tert-Butyl4-(3-cyano-2-pyridinyl)-1-piperazinecarboxylate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

2-Chloro-nicotinonitrile (2.04 g, 14.7 mmol) was added to a mixture of piperazine-1-carboxylic acid tert-butyl ester (2.74 g, 14.7 mmol) and potassium hydrogencarbonate (1.77 g, 17.6 mmol) in N,N-dimethylformamide (45 mL). The mixture was heated at 90° C. overnight. The solvent was removed and residue was partitioned between ethyl acetate and water. The organic layer was washed with water and brine then dried over magnesium sulfate and filtered. The solvent was removed to give the titled compound as an oil. 1H-NMR (400 MHz, DMSO-d6) δ 8.428 (dd, 1H); 8.08 (dd 1H); 6.95 (dd, 1H); 3.58 (m, 4H); 3.47 (m, 4H); 1.42 (s, 9H).

後処理

  1. customThe solvent was removed
  2. customresidue was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with water and brine
  4. dry with materialthen dried over magnesium sulfate
  5. filtrationfiltered
  6. customThe solvent was removed

出典と根拠

ORDレコード
ord-8b76c43a772a4f89aa7ba993427d3be0
出典データセット
uspto-grants-2010_04
特許番号
US07704997B1

反応ノート

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