1,3-Propanediamine → n-(3-Aminopropyl)benzamide

Temperatur

150 °C

Benzamide (25 g, 0.20 mol) and 1,3-diaminopropane (45.9 g, 0.60 mol) were combined in a Parr vessel and heated to 150° C. for 15 hours. The vessel was cooled and the reaction mixture was concentrated under vacuum to remove excess diamine. The residue was dissolved in water (500 mL) and concentrated hydrochloric acid was added to adjust the pH to <1. The resulting precipitate (starting benzamide and diacylated product) was removed by filtration. The filtrate was washed with dichloromethane. The aqueous layer was made strongly basic by the addition of 50% sodium hydroxide and then it was extracted with dichloromethane (4×300 mL). The extracts were combined, washed with brine (300 mL), dried over sodium sulfate and then concentrated under vacuum to provide 11.9 g of N-(3-aminopropyl)benzamide as an oil.

1. temperatureThe vessel was cooled
2. concentrationthe reaction mixture was concentrated under vacuum
3. customto remove excess diamine
4. dissolutionThe residue was dissolved in water (500 mL)
5. additionconcentrated hydrochloric acid was added
6. customThe resulting precipitate (starting benzamide and diacylated product) was removed by filtration
7. washThe filtrate was washed with dichloromethane
8. additionThe aqueous layer was made strongly basic by the addition of 50% sodium hydroxide
9. extractionit was extracted with dichloromethane (4×300 mL)
10. washwashed with brine (300 mL)
11. dry with materialdried over sodium sulfate
12. concentrationconcentrated under vacuum

ORD-Eintrag

ord-4b0fa44ee2b241e295a9ce7801e17bdd

Quelldatensatz

uspto-grants-2004_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06756382B2