Amlodipine → (2S)-2-aminobutanedioate;3-O-ethyl 5-O-methyl 2-(2-aminoethoxymethyl)-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate

HRID 2307207Notes

Reaction equation

HRID 2307207 reaction equation
[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].CC[O:31][C:32]([C:34]1C(C2C=CC=CC=2Cl)C(C(OC)=O)=C(C)[NH:36][C:35]=1[CH2:52][O:53]CCN)=[O:33].C(/C(O)=O)=C/C(O)=[O:60]>ClCCl>[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].[NH2:36][C@H:35]([C:52]([O-:53])=[O:60])[CH2:34][C:32]([O-:31])=[O:33]

Participants

4

Reactant 2

HCID 2162AmlodipineHCID 6435922Amlodipine Maleate

Product 1

HCID 86585403(2S)-2-aminobutanedioate;3-O-ethyl 5-O-methyl 2-(2-aminoethoxymethyl)-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

16 g of amlodipine and 12 g of amlodipine maleate were melted in a 300 ml flask. The melted substance was cooled to room temperature and dissolved in 300 ml of dichloromethane. The mixture was extracted with 300 ml of a 1M NaOH solution. The organic layer was discarded and the aqueous layer acidified with 55 ml of a 6 M HCl solution. The mixture was extracted with 300 ml of dichloromethane. The layers were separated and the organic layer dried over Na2SO4. The mixture was evaporated to dryness and the remaining solid recrystallised from ethanol. The obtained solid was dried in a vacuum oven at 40° C. leaving 4.7 g of an off white product.

Workup

  1. extractionThe mixture was extracted with 300 ml of a 1M NaOH solution
  2. extractionThe mixture was extracted with 300 ml of dichloromethane
  3. customThe layers were separated
  4. dry with materialthe organic layer dried over Na2SO4
  5. customThe mixture was evaporated to dryness
  6. customthe remaining solid recrystallised from ethanol
  7. customThe obtained solid was dried in a vacuum oven at 40° C.
  8. customleaving 4.7 g of an off white product

Sources & evidence

ORD record
ord-110a210c5eda48ffaf284f0109414bca
Source dataset
uspto-grants-2004_12
Patent number
US06830933B2

Reaction notes

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