반응 #992

반응 방정식

(S)-1-amino-2-propanol

potassium tertiary butoxide

2-Chloropyridine

→

title compound

수율 84.4%

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

수율 84.4%

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   기타After the exothermic reaction
2. 2
   온도the reaction was heated
3. 3
   온도under reflux overnight
4. 4
   여과filtered
5. 5
   기타to remove the potassium chloride
6. 6
   기타evaporated to an oil
7. 7
   workup.DISSOLUTIONThe crude oil was dissolved in xylene (500 ml)
8. 8
   workup.ADDITIONtoluene-p-sulphonic acid (2 g) added
9. 9
   온도heated overnight
10. 10
    온도under reflux under argon
11. 11
    추출the mixture was extracted with 2M hydrochloric acid
12. 12
    추출extracted into ethyl acetate
13. 13
    건조The ethyl acetate extracts were dried (MgSO4)
14. 14
    기타after removal of the acetic acid the product
15. 15
    workup.DISTILLATIONwas distilled

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.

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