Amlodipine → 4-(2-Chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-2-[2-(4-methyl-1-piperazinylsulphonylamino)ethoxymethyl]-1,4-dihydropyridine

HRID 280576Notes

Reaction equation

HRID 280576 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][CH2:5][C:6]1[NH:7][C:8]([CH3:28])=[C:9]([C:24]([O:26][CH3:27])=[O:25])[CH:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:23])[C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13].[CH3:29][N:30]1[CH2:35][CH2:34][N:33]([S:36](Cl)(=[O:38])=[O:37])[CH2:32][CH2:31]1>C(Cl)(Cl)Cl.C(N(CC)CC)C>[Cl:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[CH:10]1[C:9]([C:24]([O:26][CH3:27])=[O:25])=[C:8]([CH3:28])[NH:7][C:6]([CH2:5][O:4][CH2:3][CH2:2][NH:1][S:36]([N:33]2[CH2:34][CH2:35][N:30]([CH3:29])[CH2:31][CH2:32]2)(=[O:38])=[O:37])=[C:11]1[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

5

Reactant 2

HCID 2162AmlodipineHCID 111716174-methylpiperazine-1-sulfonyl Chloride

Product 1

HCID 233208274-(2-Chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-2-[2-(4-methyl-1-piperazinylsulphonylamino)ethoxymethyl]-1,4-dihydropyridineYield 43%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8471TriethylamineSolvent

Procedure

2-(2-Aminoethoxymethyl)-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine (0.5 g) was dissolved in a mixture of chloroform (dried over alumina) (20 ml) and triethylamine (2 ml) and the mixture stirred at room temperature. 4-Methyl-1-piperazinylsulphonyl chloride (0.25 g) was added in one portion and the mixture stirred at room temperature for 17 hours. After evaporation to dryness, the resultant oil was partitioned between 5% aqueous sodium carbonate and methylene chloride. The organic layer was dried (MgSO4), filtered and evaporated to give 0.3 g of a colourless oil, which was dissolved in diisopropyl ether (15 ml) and kept in a refrigerator for 14 days. The resultant crystals were collected by filtration to afford the title compound (0.1 g), m.p. 137°-139° C. Found: C, 52.58; H, 6.18; N, 9.81%. C25H35ClN4O7S requires C, 53.03; H, 6.14; N, 9.20%.

Workup

  1. stirringthe mixture stirred at room temperature for 17 hours
  2. customAfter evaporation to dryness
  3. customthe resultant oil was partitioned between 5% aqueous sodium carbonate and methylene chloride
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-6b2ac4f2f7c149bd9fd849ba8d34e5f4
Source dataset
uspto-grants-1986_05
Patent number
US04590195

Reaction notes

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