Cyclohexanone, 3,3-dimethyl- → HCID 86681322, compound

HRID 1778904Notes

Reaction equation

HRID 1778904 reaction equation
[Br:1][C:2]1[C:3]([CH3:9])=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[CH3:10][C:11]1([CH3:18])[CH2:16][CH2:15][CH2:14][C:13](=O)[CH2:12]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[Br:1][C:2]1[C:3]([CH3:9])=[C:4]([NH:5][CH:13]2[CH2:14][CH2:15][CH2:16][C:11]([CH3:18])([CH3:10])[CH2:12]2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 76322Cyclohexanone, 3,3-dimethyl-2×HCID 1235383-Bromo-o-toluidineHCID 5049666Sodium triacetoxyborohydride2×

Product 1

HCID 86681322HCID 86681322, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Bromo-2-methylaniline (1000 mg) and 3,3-dimethylcyclohexanone (780 mg) were added to dichloromethane (25 mL) and the mixture was stirred at room temperature for 15 minutes. Sodium triacetoxyborohydride (1367 mg) was then added and the solution was stirred at room temperature for 16 hours. Additional 3,3-dimethylcyclohexanone (780 mg) and sodium triacetoxyborohydride (1367 mg) were added, and the mixture was stirred for another 16 hours. The mixture was then washed with a saturated sodium bicarbonate solution and brine, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The crude material was purified on silica gel using 2.5% ethyl acetate in hexanes to provide the title compound.

Workup

  1. stirringthe solution was stirred at room temperature for 16 hours
  2. stirringthe mixture was stirred for another 16 hours
  3. washThe mixture was then washed with a saturated sodium bicarbonate solution and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe crude material was purified on silica gel using 2.5% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-2d2abee8f6ef4851be631fe5c7aef053
Source dataset
uspto-grants-2016_02
Patent number
US09266877B2

Reaction notes

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