ChemicalBook CAS DataBase List Lercanidipine hydrochloride

Lercanidipine hydrochloride synthesis

6synthesis methods

Product Name:Lercanidipine hydrochloride
CAS Number:132866-11-6
Molecular formula:C36H42ClN3O6
Molecular Weight:648.19

3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, 3-[2-[(3,3-diphenylpropyl)methylamino]-1,1-dimethylethyl] 5-methyl ester, ethanedioate (1:1)

957215-03-1

132866-11-6

The general procedure for the synthesis of 3-(1-((3,3-diphenylpropyl)(methyl)amino)-2-methylpropan-2-yl)5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate hydrochloride from the compound (CAS:957215-03-1) is as follows: 10 mmol of oxalate salt (Example 4) was dissolved in 100 mL of dichloromethane and 20 mL of aqueous solution containing 20 mmol of potassium carbonate was added. The organic phase was separated and the aqueous phase was extracted with 2 x 10 mL of dichloromethane. The organic phase was combined and treated with 20 mL of 1N hydrochloric acid solution. The organic phase was separated and concentrated. The residue was dissolved in 2,000 mL of water and 2 mL of 1N hydrochloric acid and 5 mL of saturated aqueous sodium chloride were added to form I hydrochloride hemihydrate and the product was collected by filtration. Yield: 6.2 g (95%); Purity: 99.8% (HPLC); Melting point: 118-122 ° C. HPLC conditions: RP 16 column, 125×3 mm ID, 5 μm, Detection wavelength: 233 nm; Eluent composition: 0.01 mol Na2HPO4/MeOH/acetonitrile=25/65/10; Retention time: about 15 min.

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132866-11-6
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Yield:132866-11-6 90%

Reaction Conditions:

with hydrogenchloride in diethyl ether;tert-butyl methyl etherProduct distribution / selectivity;

Steps:

3B
1.1 eq. of 2N HCl in Et₂O was added dropwise under stirring to a solution of 1 g of lercanidipine free base in 20 mL of MTBE. The precipitate formed was filtered under vacuum, rinsed with MTBE and dried under vacuum (0.15 mmHg) at 30⁰C for 4h affording a dry powder (Yield: 90%), HPLC assay: 99,6%.

References:

RECORDATI IRELAND LIMITED WO2008/15248, 2008, A1 Location in patent:Page/Page column 7

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