Potassium Carbonate → Tert-butyl 4-(3-chloropyridin-2-yl)piperazine-1-carboxylate

HRID 730705ノート

反応式

HRID 730705 の反応式
Cl[C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[N:9]1([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.[Cu]>[C:18]([O:17][C:15]([N:9]1[CH2:14][CH2:13][N:12]([C:2]2[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][N:3]=2)[CH2:11][CH2:10]1)=[O:16])([CH3:21])([CH3:19])[CH3:20]

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 169882,3-DichloropyridineHCID 143452tert-Butyl piperazine-1-carboxylate

生成物 1

HCID 11630777Tert-butyl 4-(3-chloropyridin-2-yl)piperazine-1-carboxylate

試薬・触媒・溶媒 2

HCID 23978Copper触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

A mixture of 2,3-dichloropyridine (10 g, 67.5 mmol, Aldrich), tert-butyl 1-piperazinecarboxylate (12.58 g, 67.5 mmol, Aldrich), copper powder (0.5 g, 7.8 mmol) and K2CO3 (9.33 g, 67.5 mmol) in DMF (100 mL) was stirred at 120° C. for 16 h. The reaction mixture was cooled to room temperature, concentrated in vacuo and the residue was dissolved in EtOAc (200 mL). The organic solution was washed with saturated aqueous solution of NaHCO3 (50 mL) and brine (50 mL), dried over Na2SO4, and filtered. The solvent was removed in vacuo and the residue was purified by silica gel column chromatography, eluting with 15% EtOAc/hexane, to give the title compound as an orange oil. MS (ESI, pos. ion) m/z: 298 (M+1).

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. dissolutionthe residue was dissolved in EtOAc (200 mL)
  4. washThe organic solution was washed with saturated aqueous solution of NaHCO3 (50 mL) and brine (50 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customThe solvent was removed in vacuo
  8. customthe residue was purified by silica gel column chromatography
  9. washeluting with 15% EtOAc/hexane

出典と根拠

ORDレコード
ord-8ec3d2d97ed5457598894e4b83e37840
出典データセット
uspto-grants-2009_09
特許番号
US07582761B2

反応ノート

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