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

27591-97-5

27591-69-1

2 (100 g, 0.47 mol) was mixed with 2-diethylaminoethyl chloride hydrochloride (300 g, 1.74 mol), KOH (225 g, 4.01 mol), water (320 mL), and toluene (1.5 L), and the reaction was carried out at reflux for 24 hours. After completion of the reaction, the emulsion was cooled to room temperature and the organic layer was separated. The organic layer was washed with 3 mol/L aqueous KOH (500 mL) and subsequently concentrated to dryness under vacuum. The residue was dissolved in anhydrous ethanol (420 g) and the pH was adjusted to 3.0 by passing gaseous HCl. The orange product was recrystallized by ethanol, and after filtration and drying, 200 g of tilolone hydrochloride (Compound 1) was obtained in 93% yield. The melting point of the product was 231-233°C (literature value 235-236°C [22]).IR (KBr) spectrum showed characteristic absorption peaks: 2943.3, 2596.5 (CH), 1708.9 (C=O) cm?1. ESI-MS (m/z): 411.0 [M+H]? , molecular formula C??H??N?O? (molecular weight 410.3).1H-NMR (400 MHz, D?O) chemical shift δ (ppm): 7.12 (d, J=6.5Hz, 2H), 6.99 (dd, J=6.5,1.6Hz, 2H), 6.89 (d, J=1.6Hz, 2H), 4.39 (t, J=3.6Hz , 4H), 3.68 (t, J=3.6Hz, 4H), 3.42 (q, J=5.6Hz, 8H), 1.44 (t, J=5.8Hz, 12H).

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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