1,6-2-HYDROXYBENZOYLAMINOHEXANE synthesis
- Product Name:1,6-2-HYDROXYBENZOYLAMINOHEXANE
- CAS Number:20073-95-4
- Molecular formula:C20H24N2O4
- Molecular Weight:356.42
Yield: 30%
Reaction Conditions:
for 1 h;Heating / reflux;
Steps:
Synthesis of Bis-1, 6- (2-hydroxybenzoylami.no) hexane (203):; MoI. Wt.: 356.42Scheme 1Methyl 2-hydroxybenzoate (17.6 g, 115.65 mmole) and 1,6- diaminohexane (6.4 g, 55, 32.1 mmole) were heated in a 100 mL round-bottomed flask in a heating mantle using a Dean-Stark apparatus. After 20 minutes, methanol began to distil out of the reaction mixture into the Dean-Stark apparatus. Heating was continued for 40 minutes, and thereafter the mixture was cooled to room temperature and triturated with water (100 mL) . The solid, which separated, was removed by filtration and air- dried overnight. The solid was recrystallized from alcohol which gave a first crop of the title compound (4 gm) and a second crop of 1.8 g both having mp 141-142° C (lit. mp 141- 142° C) . Total yield 5.8 g (30%) . 1H NMR (CDCl3) δ 12.30 (br s, 2H), 7.40 (m, 4H), 6.98 (d, 2H), 6.82 (t, 2H), 6.40 (br s, 2H), 3.42 (q, 4H), 1.70 (m, 4H), 1.41 (m, 4H) . The experimental method is based on a literature procedure (J. Med. Chem. (1981); 24, 1245-1249) .
References:
LIXTE BIOTECHNOLOGY HOLDINGS, INC. WO2009/45440, 2009, A1 Location in patent:Page/Page column 57
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