Reacción #992

Ecuación de reacción

(S)-1-amino-2-propanol

potassium tertiary butoxide

2-Chloropyridine

→

title compound

Rendimiento 84.4%

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

Rendimiento 84.4%

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroAfter the exothermic reaction
2. 2
   Temperaturathe reaction was heated
3. 3
   Temperaturaunder reflux overnight
4. 4
   Filtraciónfiltered
5. 5
   Otroto remove the potassium chloride
6. 6
   Otroevaporated 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
   Temperaturaheated overnight
10. 10
    Temperaturaunder reflux under argon
11. 11
    Extracciónthe mixture was extracted with 2M hydrochloric acid
12. 12
    Extracciónextracted into ethyl acetate
13. 13
    SecadoThe ethyl acetate extracts were dried (MgSO4)
14. 14
    Otroafter removal of the acetic acid the product
15. 15
    workup.DISTILLATIONwas distilled

Procedimiento

(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.

Fuente