Reaction #992

Reaction equation

(S)-1-amino-2-propanol

potassium tertiary butoxide

2-Chloropyridine

→

title compound

Yield 84.4%

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

Yield 84.4%

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   OtherAfter the exothermic reaction
2. 2
   Temperaturethe reaction was heated
3. 3
   Temperatureunder reflux overnight
4. 4
   Filtrationfiltered
5. 5
   Otherto remove the potassium chloride
6. 6
   Otherevaporated 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
   Temperatureheated overnight
10. 10
    Temperatureunder reflux under argon
11. 11
    Extractionthe mixture was extracted with 2M hydrochloric acid
12. 12
    Extractionextracted into ethyl acetate
13. 13
    DryingThe ethyl acetate extracts were dried (MgSO4)
14. 14
    Otherafter removal of the acetic acid the product
15. 15
    workup.DISTILLATIONwas distilled

Procedure

(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