Propylamine → HCID 19917483, compound

To a solution of 100 ml (1.21 mol) of n-propylamine in 170 ml of tetrahydrofuran was added 18.2 ml (0.198 mol) of 1,3-dichloropropene (E/Z=9/1) under ice cooling. The solution was stirred for 2 hours, and 1.90 g (0.01 mol) of copper (I) iodide, 709 mg (4.0 mmol) of palladium chloride, 2.10 g (8.0 mmol) of triphenylphosphine and 29.3 ml (0.238 mol) of tert-butylacetylene were added to the solution under ice cooling. The mixture was stirred for 20 hours at room temperature, and extracted with a mixture of 100 ml of ethyl acetate and 100 ml of water. The organic layer was washed with 100 ml of water. The aqueous layers were combined and extracted with 20 ml of ethyl acetate. A mixture of 200 ml of water and 6N hydrochloric acid was then added to the combined organic layers to adjust to pH 2. The aqueous layer was separated. The organic layer was extracted with 50 ml and 20 ml of water. The aqueous layers were combined, and washed with a mixture of 50 ml of ethyl acetate and 20 ml of n-hexane. The aqueous layer was treated with 200 ml of dichloromethane and then adjusted to pH 9 with 6N sodium hydroxide aqueous solution. The organic layer was separated and the aqueous layer was extracted with 20 ml of dichloromethane. The combined organic layers were washed with 50 ml of a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and treated with 17% isopropylalcohol solution of hydrogen chloride. The solvent and excess hydrogen chloride were distilled off under reduced pressure to crystallize. The crystalline residue was suspended with a mixture of 30 ml of ethyl acetate and 50 ml of n-hexane. The crystals were collected by filtration and then dried under reduced pressure to obtain 25.0 g (yield: 59%) of the above identified compound as slightly yellowish brown crystalline powder.

1. stirringThe mixture was stirred for 20 hours at room temperature
2. extractionextracted with a mixture of 100 ml of ethyl acetate and 100 ml of water
3. washThe organic layer was washed with 100 ml of water
4. extractionextracted with 20 ml of ethyl acetate
5. additionA mixture of 200 ml of water and 6N hydrochloric acid
6. additionwas then added to the combined organic layers
7. customThe aqueous layer was separated
8. extractionThe organic layer was extracted with 50 ml and 20 ml of water
9. washwashed with a mixture of 50 ml of ethyl acetate and 20 ml of n-hexane
10. additionThe aqueous layer was treated with 200 ml of dichloromethane
11. customThe organic layer was separated
12. extractionthe aqueous layer was extracted with 20 ml of dichloromethane
13. washThe combined organic layers were washed with 50 ml of a saturated aqueous solution of sodium chloride
14. dry with materialdried over anhydrous magnesium sulfate
15. additiontreated with 17% isopropylalcohol solution of hydrogen chloride
16. distillationThe solvent and excess hydrogen chloride were distilled off under reduced pressure
17. customto crystallize
18. additionThe crystalline residue was suspended with a mixture of 30 ml of ethyl acetate and 50 ml of n-hexane
19. filtrationThe crystals were collected by filtration
20. customdried under reduced pressure
21. customto obtain 25.0 g (yield: 59%) of the

ORD record

ord-d6d178b2baf84e38a2af7e3d92c716fe

Source dataset

uspto-grants-1995_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05436354