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

(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.

1. customAfter the exothermic reaction
2. temperaturethe reaction was heated
3. temperatureunder reflux overnight
4. filtrationfiltered
5. customto remove the potassium chloride
6. customevaporated to an oil
7. dissolutionThe crude oil was dissolved in xylene (500 ml)
8. additiontoluene-p-sulphonic acid (2 g) added
9. temperatureheated overnight
10. temperatureunder reflux under argon
11. extractionthe mixture was extracted with 2M hydrochloric acid
12. extractionextracted into ethyl acetate
13. dry with materialThe ethyl acetate extracts were dried (MgSO4)
14. customafter removal of the acetic acid the product
15. distillationwas distilled

ORD record

ord-1d28f93300e04c54af211412e745642b

Source dataset

uspto-grants-1998_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05723464