Methyl iodide → HCID 87523600, compound

HRID 1477196Notes

Reaction equation

HRID 1477196 reaction equation
[CH3:1][N:2]([CH3:18])[C:3]1([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)[CH2:8][CH2:7][CH:6]([CH:9]=[O:10])[CH2:5][CH2:4]1.[C:19](O[K])(C)(C)C.CI>ClCCl>[CH3:1][N:2]([CH3:18])[C:3]1([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)[CH2:8][CH2:7][C:6]([CH3:19])([CH:9]=[O:10])[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 866346814-Dimethylamino-4-(3-fluorophenyl)cyclohexanecarbaldehydeHCID 178418922HCID 178418922, compound

Product 1

HCID 87523600HCID 87523600, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the title compound of step 1 (2.73 g, 10.95 mmol) in abs. dichloromethane (50 mL) was mixed with tert-BuOK (1.47 g, 13.14 mmol) and methyl iodide (747 μl, 12 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 mixed with saturated NaCl solution (50 mL) and extracted with dichloromethane (3×30 mL). The combined organic phases were dried over Na2SO4, concentrated to low volume in a vacuum and the remaining residue was purified by flash chromatography with ethyl acetate/MeOH 20:1.

Workup

  1. custom(solid separated out)
  2. additionThe reaction mixture was mixed with saturated NaCl solution (50 mL)
  3. extractionextracted with dichloromethane (3×30 mL)
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. concentrationconcentrated to low volume in a vacuum
  6. customthe remaining residue was purified by flash chromatography with ethyl acetate/MeOH 20:1

Sources & evidence

ORD record
ord-0da8bb2b40724bed91180d189ab66977
Source dataset
uspto-grants-2016_08
Patent number
US09403767B2

Reaction notes

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