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Dimethylformamide → N-[3-(6-Dimethylaminomethyl-2-pyridyloxy)propyl]formamide

HRID 1154703
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HRID 1154703 반응식
[NH2:1][CH2:2][CH2:3][CH2:4][OH:5].[H-].[Na+].[CH3:8][N:9]([CH2:11][C:12]1[N:17]=[C:16](Cl)[CH:15]=[CH:14][CH:13]=1)[CH3:10].CN(C)[CH:21]=[O:22]>C(O)C>[CH3:8][N:9]([CH2:11][C:12]1[N:17]=[C:16]([O:5][CH2:4][CH2:3][CH2:2][NH:1][CH:21]=[O:22])[CH:15]=[CH:14][CH:13]=1)[CH3:10]
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참가 물질

6

반응물 4

HCID 6228Dimethylformamide2회HCID 90863-Amino-1-propanolHCID 24758Sodium hydrideHCID 20434272[(6-Chloropyridin-2-yl)methyl]dimethylamine

생성물 1

HCID 20434286N-[3-(6-Dimethylaminomethyl-2-pyridyloxy)propyl]formamide

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
80 °C

실험 절차

3-Aminopropanol (2.55 g, 0.034 mol) is added to a suspension of 60% sodium hydride in mineral oil (1.29 g, 0.033 mol) in dry dimethylformamide (30 ml) and the mixture is warmed to 80° C. before adding dropwise a solution of 6-dimethylaminomethyl-2-chloropyridine (5.45 g, 0.032 mol) in 30 ml of dry dimethylformamide. The reaction temperature is increased to 125° C. for 3 hours. Then the reaction is cooled, diluted with ethanol and the precipitated salts filtered. The solvents are removed under vacuum. The residue is dissolved in chloroform, washed with water, extracted into dilute hydrochloric acid and the acidic extract neutralized with sodium carbonate. The crude product is extracted into chloroform dried and evaporated (7.6 g). This residue is chromatorgrphed on silica gel (200 g) eluting with 3-8% methanol/chloroform to give 3.2 g of pure product as an oil.

후처리

  1. temperatureThe reaction temperature is increased to 125° C. for 3 hours
  2. temperatureThen the reaction is cooled
  3. filtrationthe precipitated salts filtered
  4. customThe solvents are removed under vacuum
  5. dissolutionThe residue is dissolved in chloroform
  6. washwashed with water
  7. extractionextracted into dilute hydrochloric acid
  8. extractionthe acidic extract
  9. extractionThe crude product is extracted into chloroform
  10. customdried
  11. customevaporated (7.6 g)
  12. washeluting with 3-8% methanol/chloroform

출처 및 근거

ORD 기록
ord-2c2a6c194aad4faab5c112958f1e055d
출처 데이터셋
uspto-grants-1984_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04490533

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