Propylamine → HCID 19917485, compound

To 19.7 ml (0.24 mol) of n-propylamine was added 1.82 ml (20 mmol) of 1,3-dichloropropene (E/Z =9/1) under ice cooling. The mixture was stirred for 3 hours at the same temperature, and concentrated under reduced pressure to remove n-propylamine. The residue was treated with 50 ml of ethyl acetate and precipitated n-propylamine hydrochloride was filtered and washed with 10 ml of ethyl acetate. The filtrate and washing were combined, washed with 20 ml of saturated sodium hydrogen carbonate aqueous solution and 20 ml of water and 20 ml of saturated sodium chloride aqeous solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The yellow residual oil was dissolved in 4 ml of 23% hydrogen chloride methanol solution. The solvent and excess hydrogen chloride were distilled off under reduce pressure. The resulting crystals were suspended in 8 ml of diisopropyl ether, filtered, washed with 1 ml ×2 of diisopropyl ether and then dried to obtain 2.38 g (yield 70%) of the above identified compound as slightly yellowish brown crystalline powder.

1. concentrationconcentrated under reduced pressure
2. customto remove n-propylamine
3. additionThe residue was treated with 50 ml of ethyl acetate
4. customprecipitated n-propylamine hydrochloride
5. filtrationwas filtered
6. washwashed with 10 ml of ethyl acetate
7. washThe filtrate and washing
8. washwashed with 20 ml of saturated sodium hydrogen carbonate aqueous solution and 20 ml of water and 20 ml of saturated sodium chloride aqeous solution
9. dry with materialdried over anhydrous magnesium sulfate
10. concentrationconcentrated under reduced pressure
11. dissolutionThe yellow residual oil was dissolved in 4 ml of 23% hydrogen chloride methanol solution
12. distillationThe solvent and excess hydrogen chloride were distilled off
13. filtrationfiltered
14. washwashed with 1 ml ×2 of diisopropyl ether
15. customdried
16. customto obtain 2.38 g (yield 70%) of the

ORD record

ord-8edecf1604ab43259a68946dcd7f41e1

Source dataset

uspto-grants-1995_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05436354