Tilorone dihydrochloride synthesis
- Product Name:Tilorone dihydrochloride
- CAS Number:27591-69-1
- Molecular formula:C25H36Cl2N2O3
- Molecular Weight:483.47
27591-97-5
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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]
869-24-9
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27591-69-1
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42523-29-5
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27591-69-1
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27591-97-5
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67-63-0
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27591-69-1
177 suppliers
$13.00/25mg