Methyl iodide → HCID 86634682, compound

HRID 76949Notes

Reaction equation

HRID 76949 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 86634682HCID 86634682, compound

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-800a7590af5f4f378a0508283f2064a7
Source dataset
uspto-grants-2014_09
Patent number
US08835689B2

Reaction notes

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