Réaction #992

Équation de réaction

(S)-1-amino-2-propanol

potassium tertiary butoxide

2-Chloropyridine

→

title compound

Rendement 84.4%

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

Rendement 84.4%

Solvants

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   AutreAfter the exothermic reaction
2. 2
   Températurethe reaction was heated
3. 3
   Températureunder reflux overnight
4. 4
   Filtrationfiltered
5. 5
   Autreto remove the potassium chloride
6. 6
   Autreevaporated 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
   Températureheated overnight
10. 10
    Températureunder reflux under argon
11. 11
    Extractionthe mixture was extracted with 2M hydrochloric acid
12. 12
    Extractionextracted into ethyl acetate
13. 13
    SéchageThe ethyl acetate extracts were dried (MgSO4)
14. 14
    Autreafter removal of the acetic acid the product
15. 15
    workup.DISTILLATIONwas distilled

Mode opératoire

(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.

Source