Methyl iodide → 4-Dimethylamino-1-methyl-4-phenyl-cyclohexane carbaldehyde

HRID 1477209Notes

Reaction equation

HRID 1477209 reaction equation
[CH3:1][N:2]([CH3:17])[C:3]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:8][CH2:7][CH:6]([CH:9]=[O:10])[CH2:5][CH2:4]1.[C:18](O[K])(C)(C)C.CI>ClCCl>[CH3:1][N:2]([CH3:17])[C:3]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:8][CH2:7][C:6]([CH3:18])([CH:9]=[O:10])[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 104439064-Dimethylamino-4-phenylcyclohexanecarbaldehydeHCID 178418922HCID 178418922, compound

Product 1

HCID 866346824-Dimethylamino-1-methyl-4-phenyl-cyclohexane carbaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the title compound from step 1 (11.6 g, 50.0 mmol) in abs. dichloromethane (200 mL) was mixed with tert-BuOK (6.50 g, 58.0 mmol) and methyl iodide (3.42 mL, 55.0 mmol) at 0° C. in argon. After 30 min the batch was heated to RT and then stirred overnight (solid separated out). The reaction mixture was washed with water and saturated NaCl solution (50 mL), dried over Na2SO4, concentrated to low volume in a vacuum and the remaining residue purified by flash chromatography with ethyl acetate/MeOH 20:1.

Workup

  1. custom(solid separated out)
  2. washThe reaction mixture was washed with water and saturated NaCl solution (50 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated to low volume in a vacuum
  5. customthe remaining residue purified by flash chromatography with ethyl acetate/MeOH 20:1

Sources & evidence

ORD record
ord-d007b93799a44017a471782931aed507
Source dataset
uspto-grants-2016_08
Patent number
US09403767B2

Reaction notes

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