Nisoldipine synthesis
- Product Name:Nisoldipine
- CAS Number:63675-72-9
- Molecular formula:C20H24N2O6
- Molecular Weight:388.41
61312-59-2
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63675-72-9
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Yield:63675-72-9 52.9%
Reaction Conditions:
with dmap in cyclohexane at 75 - 85; for 26 h;Heating / reflux;
Steps:
2 Example 2; synthesis of [NISOLDIPINE]
A reactor was fed with isobutyl 2-2 (nitrobenzylidene) acetoacetate (22 kg; 0.0755 [KMOL),] 4-dimethylaminopyridine (0,55 kg), methyl 3-aminocrotonate (6.1 kg; 0.053 [KMOL),] cyclohexane (88 kg). The mass was [REFLUXED] [(75°-85°C)] for a period of 10 hrs, then an additional amount of methyl 3-aminocrotonate (6.1 kg) was added. The reaction mass was refluxed [(75°-85C°)] for 16 hrs at least (during the reaction the product precipitated). Distillation was performed in plenum at an internal temperature of [85°C] max, until formation of a pasty but [STIRRABLE] residue. The residue was cooled to [20°-30°C] ; distilled water (11 kg) and methanol (66 kg) were added. The mixture was stirred at [20°-30°C] for a period of 15 min, cooled to [10°-15°C] with stirring for 30 min at least, centrifuged and washed with methanol (16.5 kg) and then with distilled water (16.5 kg). The wet solid obtained (crude [NISOLDIPINE)] was fed to a rector, added with acetone (77 kg), stirred at [20°-30°C] until dissolution, added with distilled water (40.5 kg), kept under stirring at [20°-30°C] for 1 hr at least, until complete precipitation. An additional amount of distilled water (9.5 kg) was added at [20°-] [25°C.] The mixture was maintained under stirring at [20°-25°C] for an additional 1 hr and centrifuged. The final solid was washed with an acetone (16.5 kg)/distilled water (16.5 kg) mixture prepared separately, and then with distilled water (22 kg). The solid was dried at [40°-50°C] to give 15.5 kg dried [NISOLDIPINE] product with a degree of purity of over 99.7% (HPLC). Yield 52.9%.
References:
ERREGIERRE, S.P.A. WO2004/2958, 2004, A1 Location in patent:Page 4-5
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63675-72-9
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