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

HRID 336598

Reaction equation

HRID 336598 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-7c8f4e9fc1fb4d9b8c9f8978a82eb989
Source dataset
uspto-grants-2014_11
Patent number
US08889675B2

Linked notes

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