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 1359511Notes

Reaction equation

HRID 1359511 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 are melted in a 300 ml flask. The melted substance is cooled to room temperature and dissolved in 300 ml of dichloromethane. The mixture is extracted with 300 ml of a 1M NaOH solution. The organic layer is discarded and the aqueous layer acidified with 55 ml of a 6 M HCl solution. The mixture is extracted with 300 ml of dichloromethane. The layers are separated and the organic layer dried over Na2SO4. The mixture is evaporated to dryness and the resulting waxy solid recrystallized from ethanol. The obtained sticky solid is dried in a vacuum oven at 40° C. leaving 4.7 g of an off white product.

Workup

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

Sources & evidence

ORD record
ord-136a5f2dffca4fdf81996f49288e4259
Source dataset
uspto-grants-2003_07
Patent number
US06600047B2

Reaction notes

Loading…