Nifedipine → N-Methylnifedipine

HRID 481699Notes

Reaction equation

HRID 481699 reaction equation
[CH3:1][C:2]1[NH:7][C:6]([CH3:8])=[C:5]([C:9]([O:11][CH3:12])=[O:10])[CH:4]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=2[N+:19]([O-:21])=[O:20])[C:3]=1[C:22]([O:24][CH3:25])=[O:23].[H-].[Na+].CI.[C:30](OCC)(=O)C>O1CCCC1>[CH3:1][C:2]1[N:7]([CH3:30])[C:6]([CH3:8])=[C:5]([C:9]([O:11][CH3:12])=[O:10])[CH:4]([C:13]2[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:3]=1[C:22]([O:24][CH3:25])=[O:23]

Participants

6

Reactant 4

HCID 4485NifedipineHCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 24758Sodium hydride

Product 1

HCID 14817573N-Methylnifedipine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

12 g nifedipine was introduced into a 100-mL three-neck flask and dissolved in 50 mL tetrahydrofuran under nitrogen. 1.66 g of a 60% dispersion of sodium hydride in oil was then added with stirring. After stirring for a short period of time, 10 mL methyl iodide was added and the reaction was stirred for 1 hour at 38° C. 200 mL ethyl acetate was then added, and the organic layer was thereafter washed several times with water and dried over sodium sulfate. The sodium sulfate was subsequently filtered off and the solvent was then pulled off from the filtrate on a rotary evaporator. The obtained solid was dissolved in 200 mL MIBK, and the addition of hexane to this solution then yielded 8.9 g N-methylnifedipine as yellow crystals. mp=184°-187° C.

Workup

  1. additionwas added
  2. stirringthe reaction was stirred for 1 hour at 38° C
  3. washthe organic layer was thereafter washed several times with water
  4. dry with materialdried over sodium sulfate
  5. filtrationThe sodium sulfate was subsequently filtered off
  6. customthe solvent was then pulled off from the filtrate on a rotary evaporator
  7. dissolutionThe obtained solid was dissolved in 200 mL MIBK
  8. additionthe addition of hexane to this solution

Sources & evidence

ORD record
ord-9e690fa295b54e4a9c2949377669dc5d
Source dataset
uspto-grants-1998_08
Patent number
US05789460

Reaction notes

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