2-Chloropyridine → (S)-N-(2-pyridyl)-1-amino-2-propanol

HRID 368701

반응식

HRID 368701 반응식
[NH2:1][CH2:2][C@@H:3]([OH:5])[CH3:4].CC(C)([O-])C.[K+].Cl[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1>O1CCCC1>[N:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[NH:1][CH2:2][C@@H:3]([OH:5])[CH3:4]

참가 물질

5

반응물 3

HCID 79772-ChloropyridineHCID 7311736(S)-(+)-1-Aminopropan-2-olHCID 23665647Potassium tert-butoxide

생성물 1

HCID 820205(S)-N-(2-pyridyl)-1-amino-2-propanol수율 84.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

(S)-1-amino-2-propanol (43 g, 0.57M) was added to a stirred solution of potassium tertiary butoxide (64.2 g, 0.66M) in tetrahydrofuran (500 ml). 2-Chloropyridine (65.1 g 0.66M) was then added dropwise. After the exothermic reaction had subsided, the reaction was heated under reflux overnight, filtered to remove the potassium chloride and evaporated to an oil. The crude oil was dissolved in xylene (500 ml) and toluene-p-sulphonic acid (2 g) added and heated overnight under reflux under argon. After cooling to room temperature, the mixture was extracted with 2M hydrochloric acid. The acid extracts were basified with 2M sodium hydroxide and extracted into ethyl acetate. The ethyl acetate extracts were dried (MgSO4) and after removal of the acetic acid the product was distilled affording 73.5 g of the title compound, bp 100-110° C. at 0.2 mbar.

후처리

  1. customAfter the exothermic reaction
  2. temperaturethe reaction was heated
  3. temperatureunder reflux overnight
  4. filtrationfiltered
  5. customto remove the potassium chloride
  6. customevaporated to an oil
  7. dissolutionThe crude oil was dissolved in xylene (500 ml)
  8. additiontoluene-p-sulphonic acid (2 g) added
  9. temperatureheated overnight
  10. temperatureunder reflux under argon
  11. extractionthe mixture was extracted with 2M hydrochloric acid
  12. extractionextracted into ethyl acetate
  13. dry with materialThe ethyl acetate extracts were dried (MgSO4)
  14. customafter removal of the acetic acid the product
  15. distillationwas distilled

출처 및 근거

ORD 기록
ord-d7ce8422641b4e80ace152903ee395e8
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06133449

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