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Potassium Carbonate → 6-chloro-3-nitro-N-(3-piperidin-1-ylpropyl)pyridin-2-amine

HRID 1727035
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HRID 1727035 반응식
C(=O)([O-])[O-].[K+].[K+].[N:7]1([CH2:13][CH2:14][CH2:15][NH2:16])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.Cl[C:18]1[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][CH:21]=[C:20]([Cl:27])[N:19]=1>C1(C)C=CC=CC=1>[Cl:27][C:20]1[N:19]=[C:18]([NH:16][CH2:15][CH2:14][CH2:13][N:7]2[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][CH:21]=1
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참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 19049Piperidine-1-propylamineHCID 852392,6-Dichloro-3-nitropyridine

생성물 1

HCID 860008436-chloro-3-nitro-N-(3-piperidin-1-ylpropyl)pyridin-2-amine수율 61%

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
20 °C

실험 절차

Potassium carbonate (540 mg, 1.5 eq) and 3-piperidino-propylamine (420 mg, 1 eq) are added successively to 2,6-dichloro-3-nitropyridine (500 mg, 1 eq) in solution in toluene (10 ml). After stirring for 2 hours at a temperature of approximately 20° C., the mixture is concentrated under reduced pressure at 40° C. then water (20 ml) and dichloromethane (70 ml) are added. After decantation and extractions, the combined organic phases are washed with salt water, dried over Na2SO4 then concentrated under reduced pressure at 40° C. Purification of the solid obtained, by flash chromatography on silica gel (eluent: heptane/ethyl acetate 3:7 to 100% ethyl acetate), produces the expected compound in the form of a yellow solid (473 mg; 61% yield).

후처리

  1. concentrationthe mixture is concentrated under reduced pressure at 40° C.
  2. additionwater (20 ml) and dichloromethane (70 ml) are added
  3. extractionAfter decantation and extractions
  4. washthe combined organic phases are washed with salt water
  5. dry with materialdried over Na2SO4
  6. concentrationthen concentrated under reduced pressure at 40° C
  7. customPurification of the solid
  8. customobtained, by flash chromatography on silica gel (eluent: heptane/ethyl acetate 3:7 to 100% ethyl acetate)

출처 및 근거

ORD 기록
ord-72809767555d4c14904f18cf70924148
출처 데이터셋
uspto-grants-2009_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07495009B2

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