ChemicalBook CAS DataBase List Tilorone dihydrochloride

Tilorone dihydrochloride synthesis

4synthesis methods

Product Name:Tilorone dihydrochloride
CAS Number:27591-69-1
Molecular formula:C25H36Cl2N2O3
Molecular Weight:483.47

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27591-69-1
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Yield:27591-69-1 200 g

Reaction Conditions:

with hydrogenchloride in ethanol; pH=3

Steps:

2,7-bis[2-(Diethylamino)ethoxy]-9H-fluoren-9-one hydrochloride (1)
A mixture of 2 (100 g, 0.47 mol),2-diethylaminoethyl chloride hydrochloride (300 g, 1.74 mol), KOH (225 g, 4.01 mol), water (320 mL)and toluene (1.5 L) was refluxed for 24 h. The emulsion was cooled, and then organic layer was separated, washed with KOH aq. (3 mol/L, 500 mL) and concentrated up to dryness in vacuum. The residue was dissolved in anhydrous ethanol (420 g) and acidified with gasified HCl to pH 3.0. The orange product was recrystallized with ethanol, filtered, and dried to give 200 g of compound 1 in a yield of 93%; m.p. 231-233 °C (Lit. 235-236 C [22]); IR (KBr), ν (cm1): 2943.3, 2596.5 (CH), 1708.9(C=O); ESI-MS (m/z): 411.0 [M + H]+, C25H34N2O3 (MW. = 410.3); 1H-NMR (400 MHz, D2O), δ (ppm):7.12 (d, J = 6.5 Hz, 2H), 6.99 (dd, J = 6.5, 1.6 Hz, 2H), 6.89 (d, J = 1.6 Hz, 2H), 4.39 (t, J = 3.6 Hz,4H), 3.68(t, J = 3.6 Hz, 4H), 3.42 (q, J = 5.6 Hz, 8H), 1.44 (t, J = 5.8 Hz, 12H).

References:

Zhang, Junren;Yao, Qizheng;Liu, Zuliang;De Sousa, Maria Emília [Molecules,2015,vol. 20,# 12,p. 21458 - 21463]

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869-24-9 Synthesis