Ethanol → Amlodipine Maleate

HRID 543141Notes

Reaction equation

HRID 543141 reaction equation
[N:1]([CH2:4][CH2:5][O:6][CH2:7][C:8]1[NH:9][C:10]([CH3:30])=[C:11]([C:26]([O:28][CH3:29])=[O:27])[CH:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[Cl:25])[C:13]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N+]=[N-].[H][H].C([OH:35])C>[Pd]>[C:7]([OH:6])(=[O:35])/[CH:8]=[CH:13]\[C:14]([OH:16])=[O:15].[NH2:1][CH2:4][CH2:5][O:6][CH2:7][C:8]1[NH:9][C:10]([CH3:30])=[C:11]([C:26]([O:28][CH3:29])=[O:27])[CH:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[Cl:25])[C:13]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

5

Reactant 3

HCID 702EthanolHCID 30926063-O-ethyl 5-O-methyl 2-(2-azidoethoxymethyl)-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 6435922Amlodipine Maleate

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A suspension of 2-(2-azidoethoxymethyl)-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine (103 g) in ethanol (2.5 l) was stirred for 16 hours at room temperature under one atmosphere of hydrogen in the presence of 5% palladium on calcium carbonate (40 g). The reaction mixture was filtered and evaporated and the residue treated with a solution of maleic acid (22 g) in ethanol (100 ml). The reaction mixture was stirred at room temperature for 2 hours and then the resulting solid collected, washed with ethanol, and dried to give the title compound (100 g), m.p. 169°-170.5°.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customevaporated
  3. additionthe residue treated with a solution of maleic acid (22 g) in ethanol (100 ml)
  4. customthe resulting solid collected
  5. washwashed with ethanol
  6. customdried

Sources & evidence

ORD record
ord-d1d71c1bdfbd4862a08911437dca0bb9
Source dataset
uspto-grants-1987_04
Patent number
US04661485

Reaction notes

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