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

HRID 912763

반응식

HRID 912763 반응식
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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 23978Copper촉매HCID 6228Dimethylformamide용매

반응 조건

온도
120 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-525e89e0db04423b8ae69121722b1efc
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08026241B2

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