Dichloromethane → N-(3-bromo-2-methylphenyl)tricyclo[3.3.1.13,7]decane-1-carboxamide

HRID 588675Notes

Reaction equation

HRID 588675 reaction equation
[Br:1][C:2]1[C:3]([CH3:9])=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].C(N(C(C)C)CC)(C)C.ClCCl.[C:22]12([C:32](Cl)=[O:33])[CH2:31][CH:26]3[CH2:27][CH:28]([CH2:30][CH:24]([CH2:25]3)[CH2:23]1)[CH2:29]2>C(OCC)(=O)C>[Br:1][C:2]1[C:3]([CH3:9])=[C:4]([NH:5][C:32]([C:22]23[CH2:31][CH:26]4[CH2:25][CH:24]([CH2:30][CH:28]([CH2:27]4)[CH2:29]2)[CH2:23]3)=[O:33])[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 81531DiisopropylethylamineHCID 989151-Adamantanecarbonyl chlorideHCID 1235383-Bromo-o-toluidine

Product 1

HCID 86681266N-(3-bromo-2-methylphenyl)tricyclo[3.3.1.13,7]decane-1-carboxamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3-Bromo-2-methylaniline (800 mg) and diisopropylethylamine (1667 mg) were added to dichloromethane (12 mL). 1-Adamantanecarbonyl chloride (940 mg) was added and the solution was stirred at room temperature for 16 hours. The solution was diluted with 50% ethyl acetate (hexanes), washed three times with 1 M aqueous HCl, washed with brine, dried over anhydrous sodium sulfate, and filtered. The solvent volume was partially reduced under vacuum, and the solid material precipitated out of solution, which was isolated by filtration to provide the title compound.

Workup

  1. washwashed three times with 1 M aqueous HCl
  2. washwashed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customthe solid material precipitated out of solution
  6. customwhich was isolated by filtration

Sources & evidence

ORD record
ord-130d84c268cc4388b118127c1e9a60bf
Source dataset
uspto-grants-2016_01
Patent number
US09227963B2

Reaction notes

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