Nifedipine → N-Methylnifedipine

HRID 343269Notes

Reaction equation

HRID 343269 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 placed in a 100-mL three-neck flask and dissolved in 50 mL tetrahydrofuran under nitrogen. To this was added 1.66 g of an oil dispersion of sodium hydride (60% NaH) with stirring. After stirring for a brief 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 washed several times with water and dried over sodium sulfate. The sodium sulfate was filtered off and the solvent was removed from the filtrate on a rotary evaporator. The resulting solid was dissolved in 200 mL MIBK. The addition of hexane gave 8.9 g N-methylnifedipine as yellow crystals.

Workup

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

Sources & evidence

ORD record
ord-2b89285e65764e26bd9d403ab29d233b
Source dataset
uspto-grants-1999_01
Patent number
US05861235

Reaction notes

Loading…