Methyl iodide → Methyl 4-[(methylamino)methyl]benzoate

HRID 605580Notes

Reaction equation

HRID 605580 reaction equation
[H-].[Na+].CI.C(O[C:10]([NH:12][CH2:13][C:14]1[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:15]=1)=O)(C)(C)C>C1COCC1>[CH3:10][NH:12][CH2:13][C:14]1[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 14221817Methyl 4-((((1,1-dimethylethoxy)carbonyl)amino)methyl)benzoate

Product 1

HCID 11194668Methyl 4-[(methylamino)methyl]benzoateYield 65.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.13 g of NaH at 60% in oil, and then 2.35 ml of methyl iodide are added to a solution of 5 g of methyl 4-[[(tert-butoxycarbonyl)amino]methyl]benzoate in 150 ml of THF and the mixture is left to stir at AT overnight. The reaction mixture is concentrated under vacuum, the residue is taken up with a water/ice mixture, the mixture is extracted with EtOAc, the organic phase is dried over Na2SO4, and the solvent is evaporated off under vacuum. The residue is taken up with 80 ml of 2N hydrochloric ether, 1 ml of water is added, and the mixture is left to stir at AT overnight. The reaction mixture is concentrated under vacuum, the residue is taken up with a 5% NaHCO3 solution, the mixture is extracted with DCM, the organic phase is dried over Na2SO4, and the solvent is evaporated off under vacuum. 2.2 g of the expected compound are obtained.

Workup

  1. waitthe mixture is left
  2. concentrationThe reaction mixture is concentrated under vacuum
  3. extractionthe mixture is extracted with EtOAc
  4. dry with materialthe organic phase is dried over Na2SO4
  5. customthe solvent is evaporated off under vacuum
  6. additionis added
  7. waitthe mixture is left
  8. stirringto stir at AT overnight
  9. concentrationThe reaction mixture is concentrated under vacuum
  10. extractionthe mixture is extracted with DCM
  11. dry with materialthe organic phase is dried over Na2SO4
  12. customthe solvent is evaporated off under vacuum

Sources & evidence

ORD record
ord-e7ac8cffd9414eca9217c6812286fcd2
Source dataset
uspto-grants-2011_03
Patent number
US07915258B2

Reaction notes

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