Methyl iodide → HCID 87523600, compound

HRID 76936Notes

Reaction equation

HRID 76936 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-e70c76a067b54bb0a5a0b16c9e445d86
Source dataset
uspto-grants-2014_09
Patent number
US08835689B2

Reaction notes

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