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 ever 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 reduced 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 ever 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 under reduced pressure
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-ec270d059e104377adc1df64832ee1a6

Source dataset

uspto-grants-1995_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05440049