CIS-4-(4-METHYL-PIPERAZIN-1-YL)-4-OXO-BUT-2-ENOIC ACID synthesis
- Product Name:CIS-4-(4-METHYL-PIPERAZIN-1-YL)-4-OXO-BUT-2-ENOIC ACID
- CAS Number:42574-70-9
- Molecular formula:C9H14N2O3
- Molecular Weight:198.22
109-01-3
677 suppliers
$5.00/5G
108-31-6
885 suppliers
$13.47/50g
42574-70-9
13 suppliers
$45.00/10mg
Yield:42574-70-9 82%
Reaction Conditions:
in diethyl ether at 20; for 2 h;
Steps:
Synthesis of monoamides of maleic acid 1a-k: (Z)-4-(4-methylpiperazin-1-yl)-4-oxobut-2-enoic acid (1i)
1-Methylpiperazine (1.664 mL, 15 mmol) was added dropwise to a strirred solution of maleic anhydride (1.471 g, 15 mmol) in diethyl ether (75 mL) at room temperature. After 2 h, the solvent was evaporated under vacuum, the resulting oil was triturated with CH3CN. The precipitated product was filtered and washed with CH3CN (5 mL). White powder, yield 2.428 g (82%), mp 195.5-196 °C (CH3CN); IR (KBr) ν 3440, 1620, 1444, 1408, 1322, 1259, 971 cm-1; 1H NMR (300 MHz, DMSO-d6) δ (ppm) 2.20 (s, 3H), 2.32 (t, J=5.0 Hz, 4H), 3.33 (t, J=5.0 Hz, 2H), 3.46 (t, J=5.0 Hz, 2H), 5.94 (d, J=12.0 Hz, 1H), 6.60 (d, J=12.0 Hz, 1H); 13C NMR (75.5 MHz, D2O) δ (ppm) 38.6, 43.1, 43.6, 52.6, 52.9, 128.9, 133.0, 170.2, 172.7; MS-ES m/z 197 ([M-H]-, 100%). Anal. Calcd for C9H14N2O3: C, 54.53; H, 7.12; N, 14.13. Found: C, 54.41; H, 7.29; N, 14.09.
References:
Majce, Vita;Ko?evar, Marijan;Polanc, Slovenko [Tetrahedron Letters,2011,vol. 52,# 26,p. 3287 - 3290] Location in patent:supporting information; experimental part
109-01-3
677 suppliers
$5.00/5G
108-31-6
885 suppliers
$13.47/50g
42574-70-9
13 suppliers
$45.00/10mg
129795-76-2
2 suppliers
inquiry