Reaktion #992

Reaktionsgleichung

(S)-1-amino-2-propanol

potassium tertiary butoxide

2-Chloropyridine

→

title compound

Ausbeute 84.4%

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

Ausbeute 84.4%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAfter the exothermic reaction
2. 2
   Temperaturthe reaction was heated
3. 3
   Temperaturunder reflux overnight
4. 4
   Filtrationfiltered
5. 5
   Sonstigeto remove the potassium chloride
6. 6
   Sonstigeevaporated 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
   Temperaturheated overnight
10. 10
    Temperaturunder reflux under argon
11. 11
    Extraktionthe mixture was extracted with 2M hydrochloric acid
12. 12
    Extraktionextracted into ethyl acetate
13. 13
    TrocknenThe ethyl acetate extracts were dried (MgSO4)
14. 14
    Sonstigeafter removal of the acetic acid the product
15. 15
    workup.DISTILLATIONwas distilled

Vorschrift

(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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