Methyl iodide → HCID 70873902, compound

HRID 2208943Notes

Reaction equation

HRID 2208943 reaction equation
[CH2:1]([N:3]([CH:15]1[CH2:20][CH2:19][C:18]([OH:22])([CH3:21])[CH2:17][CH2:16]1)[C:4]1[C:5]([CH3:14])=[C:6]([CH:11]=[CH:12][CH:13]=1)[C:7]([O:9][CH3:10])=[O:8])[CH3:2].[H-].[Na+].[CH3:25]I>C1COCC1>[CH2:1]([N:3]([CH:15]1[CH2:16][CH2:17][C:18]([O:22][CH3:25])([CH3:21])[CH2:19][CH2:20]1)[C:4]1[C:5]([CH3:14])=[C:6]([CH:11]=[CH:12][CH:13]=1)[C:7]([O:9][CH3:10])=[O:8])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 70874132HCID 70874132, compound

Product 1

HCID 70873902HCID 70873902, compoundYield 95.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled solution of methyl 3-(ethyl(4-hydroxy-4-methylcyclohexyl)amino)-2-methylbenzoate (300 mg, 0.98 mmol) in THF (5 ml), was added sodium hydride (235 mg, 5.89 mmol) portion-wise followed by methyl iodide (0.61 ml, 9.8 mmol). The mixture was stirred at room temperature for 1 h, cooled to 0° C. quenched with ice cold water and extracted with ethyl acetate. The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure to give 300 mg of the crude title compound.

Workup

  1. temperaturecooled to 0° C.
  2. customquenched with ice cold water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-07e18e5ae02f451992abc8d2cf819986
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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