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Triethylamine → N-(2-aminoethyl)pyridine-2-carboxamide

HRID 34951
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HRID 34951 반응식
O[CH2:2][CH2:3][NH:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1)=[O:6].C([N:15](CC)CC)C>C(Cl)Cl>[NH2:15][CH2:2][CH2:3][NH:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1)=[O:6]
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참가 물질

4

반응물 2

HCID 8471TriethylamineHCID 2045999N-(2-Hydroxyethyl)picolinamide

생성물 1

HCID 3152207N-(2-aminoethyl)pyridine-2-carboxamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

3.0 g of N-(2-hydroxyethyl)pyridine-2-carboxamide were placed in a round flask with 20 ml of methylene chloride and 2.5 ml of triethylamine and the mixture was cooled to 0°-5°. A solution of 1.4 ml of methanesulfochloride in 30 ml of methylene chloride was added dropwise thereto while cooling well at 0°-5°. The reaction mixture was stirred at 0°-5° for a further 2 hours and thereafter added dropwise at 0°-5° to 30 ml of concentrated (25%) ammonia. The reaction mixture was stirred at room temperature overnight and thereafter concentrated under reduced pressure. The residue was dissolved in methylene chloride, extracted with 2N hydrochloric acid and washed with water. The aqueous extracts were combined, made basic with concentrated (28%) sodium hydroxide solution and extracted 3 times with methylene chloride. The organic extracts were dried over magnesium sulfate, filtered and evaporated. There was obtained a yellow oil which was chromatographed on silica gel for further purification. As the elution agent there was used firstly ethyl acetate, thereafter an ethyl acetate/alcohol mixture and finally alcohol. There was obtained N-(2-aminoethyl)pyridine-2-carboxamide which, in accordance with thin-layer chromatography, was identical with the compound described in Example 1.

후처리

  1. temperaturethe mixture was cooled to 0°-5°
  2. temperaturewhile cooling well at 0°-5°
  3. additionadded dropwise at 0°-5° to 30 ml
  4. concentrationof concentrated (25%) ammonia
  5. stirringThe reaction mixture was stirred at room temperature overnight
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe residue was dissolved in methylene chloride
  8. extractionextracted with 2N hydrochloric acid
  9. washwashed with water
  10. concentrationwith concentrated (28%) sodium hydroxide solution
  11. extractionextracted 3 times with methylene chloride
  12. dry with materialThe organic extracts were dried over magnesium sulfate
  13. filtrationfiltered
  14. customevaporated
  15. customThere was obtained a yellow oil which
  16. customwas chromatographed on silica gel for further purification

출처 및 근거

ORD 기록
ord-0a0295752cdb423dacbfd62f90ae444e
출처 데이터셋
uspto-grants-1988_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04764522

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