Nicotinic Acid → 3-O-ethyl 5-O-methyl 2-(2-aminoethoxymethyl)-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate;pyridine-3-carboxylate

HRID 47598

Reaction equation

HRID 47598 reaction equation
[CH3:1][CH2:2][O:3][C:4]([C:6]1[CH:11]([C:12]2[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:10]([C:19]([O:21][CH3:22])=[O:20])=[C:9]([CH3:23])[NH:8][C:7]=1[CH2:24][O:25][CH2:26][CH2:27][NH2:28])=[O:5].[C:29]([OH:37])(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[N:32][CH:31]=1>C(O)C>[CH3:1][CH2:2][O:3][C:4]([C:6]1[CH:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=2[Cl:18])[C:10]([C:19]([O:21][CH3:22])=[O:20])=[C:9]([CH3:23])[NH:8][C:7]=1[CH2:24][O:25][CH2:26][CH2:27][NH2:28])=[O:5].[C:29]([O-:37])(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[N:32][CH:31]=1

Participants

4

Reactant 2

HCID 938Nicotinic AcidHCID 2162Amlodipine2×

Product 1

HCID 865903903-O-ethyl 5-O-methyl 2-(2-aminoethoxymethyl)-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate;pyridine-3-carboxylateYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

Amlodipine free base (4.09 g) was added to 40 mL of ethanol. The mixture was heated at reflux and stirred until the solid was completely dissolved. Nicotinic acid (1.23 g) was added to the amlodipine solution and then the mixture was slowly cooled down to 0° C. within one hour. The solids formed were isolated by filtration, washed with ethyl acetate and dried under reduced pressure to yield 4.51 g of amlodipine nicotinate.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux
  3. dissolutionwas completely dissolved
  4. customThe solids formed
  5. customwere isolated by filtration
  6. washwashed with ethyl acetate
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-08d6d8aa25df402e84fb3648a2237202
Source dataset
uspto-grants-2004_03
Patent number
US06699892B2

Linked notes

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