Potassium Hydroxide → HCID 54387005, compound

HRID 486604Notes

Reaction equation

HRID 486604 reaction equation
C[O:2][C:3]([C:5]1[CH:10]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=2)[C:9]([C:21]([O:23][CH3:24])=[O:22])=[C:8]([CH3:25])[N:7]([CH2:26][CH2:27][CH2:28][O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:6]=1[CH3:37])=[O:4].[OH-].[K+]>CS(C)=O.O>[CH3:24][O:23][C:21]([C:9]1[CH:10]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=2)[C:5]([C:3]([OH:4])=[O:2])=[C:6]([CH3:37])[N:7]([CH2:26][CH2:27][CH2:28][O:29][CH2:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:8]=1[CH3:25])=[O:22]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 10369042HCID 10369042, compound

Product 1

HCID 54387005HCID 54387005, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

After 2.15 g (4.2 mmols) of 1,4-dihydro-4-(3,4-dimethoxy-phenyl)-2,6-dimethyl-1-(3-benzyloxypropyl)-3,5-pyridine-dicarboxylic acid 3,5-dimethyl ester prepared by the process described in Japanese Patent Application Laid Open No. 1-316357 was dissolved in 8 ml of dimethylsulfoxide, 320 mg (4.9 mmols) of potassium hydroxide dissolved in 0.5 ml of water was added to the solution. The mixture was heated at 100° C. for 5 hours. After the solvent was distilled off under reduced pressure, 10 ml of water was added to the residue followed by extraction twice with ethyl acetate. After the aqueous phase was rendered acidic with diluted hydrochloric acid, extraction was performed 3 times with chloroform. After washing with water, the extract was concentrated and the obtained residue was purified by silica gel column chromatography (developing solvent: ethyl acetate-n-hexane=1:1) to give 875 mg of 1,4-dihydro-4-(3,4-dimethoxyphenyl)-2,6-dimethyl-1-(3-benzyloxypropyl)-3,5-pyridinedicarboxylic acid 3-methyl ester as an oil. Yield, 42%. The obtained monocarboxylic acid was esterified by the method described in Example 1 to give 1,4-dihydro-4-(3,4-dimethoxyphenyl)-2,6-dimethyl-1-(3-benzyloxypropyl)-3,5-pyridine-dicarboxylic acid 3-methyl-5-[3 -(4-methylpiperazino)propyl] ester.

Workup

  1. additionwas added to the solution
  2. distillationAfter the solvent was distilled off under reduced pressure, 10 ml of water
  3. additionwas added to the residue
  4. extractionfollowed by extraction twice with ethyl acetate
  5. extractionAfter the aqueous phase was rendered acidic with diluted hydrochloric acid, extraction
  6. washAfter washing with water
  7. concentrationthe extract was concentrated
  8. customthe obtained residue was purified by silica gel column chromatography (developing solvent: ethyl acetate-n-hexane=1:1)

Sources & evidence

ORD record
ord-07626d353958469cb6e783def7dd8827
Source dataset
uspto-grants-1994_03
Patent number
US05292757

Reaction notes

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