Spermidine trihydrochloride synthesis

6synthesis methods

Product Name:Spermidine trihydrochloride
CAS Number:334-50-9
Molecular formula:C7H22Cl3N3
Molecular Weight:254.63

Carbamic acid, N-[4-[[3-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)propyl]amino]butyl]-, 1,1-dimethylethyl ester

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Yield:334-50-9 78.9%

Reaction Conditions:

Stage #1: tert-butyl {4-{[3-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)propyl]amino}butyl}carbamatewith hydrazine hydrate in ethanol; for 4 h;Reflux;Large scale;
Stage #2: with hydrogenchloride in ethanol;water;Reflux;Large scale;Reagent/catalyst;

Steps:

5-6 Example 6: Preparation of spermidine trihydrochloride (II)

Dissolve 28kg of N-tert-butoxycarbonyl-4-(3-phthalimidopropylamino)butylamine (III) in 120L of absolute ethanol, and then slowly add 80% hydrazine hydrate 9.0 After the kg was added, the temperature was raised to reflux, and the reaction was kept warm for 4 hours. LCMS monitored that the reaction of the raw materials had been converted into intermediates.Then add 100kg of 36% concentrated hydrochloric acid (note that gas is generated when hydrochloric acid is added), then add it to room temperature and solid precipitate out, stir overnight, filter, rinse with a small amount of water, and concentrate the filtrate under reduced pressure to 65°C without any liquid, add 100L without Water ethanol, heated and refluxed for 30 minutes, cooled to room temperature, suction filtered after 2 hours, rinsed with a small amount of ethanol, and dried to obtain solid spermidine trihydrochloride (II) 15.0kg, purity: 85.3%, molar yield: 78.9 %.

References:

CN113548971,2021,A Location in patent:Paragraph 0047-0053

83392-10-3 Synthesis