Methane → HCID 22992881, compound

HRID 1168619Notes

Reaction equation

HRID 1168619 reaction equation
[CH3:1][C:2]1([CH3:8])[CH2:6][C:5](=O)[CH:4]=[CH:3]1.[CH2:9]([NH2:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C>C(O)C.[Pt]=O>[CH3:1][C:2]1([CH3:8])[CH2:3][CH2:4][CH:5]([NH:16][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:6]1

Participants

6

Reactant 3

HCID 297MethaneHCID 7504BenzylamineHCID 1409554,4-Dimethyl-2-cyclopenten-1-one

Product 1

HCID 22992881HCID 22992881, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

4,4-Dimethyl-2-cyclopenten-1-one (804 mg, 7.30 mmol) and benzylamine (877 μL, 8.03 mmol) were dissolved in 15 mL of ethanol. Charcoal (400 mg) and platinum oxide (Adams' catalyst, 331 mg, 1.46 mmol) were added and the mixture was stirred under hydrogen (balloon) for 24 hours. The reaction was purged with argon and diluted with ethyl acetate. The mixture was loaded onto silica gel and purified by flash chromatography on silica gel eluted with 5% triethylamine and hexane to provide 1.24 g (84%) of a clear colorless oil.

Workup

  1. customThe reaction was purged with argon
  2. additiondiluted with ethyl acetate
  3. custompurified by flash chromatography on silica gel
  4. washeluted with 5% triethylamine and hexane

Sources & evidence

ORD record
ord-25b3a64ab84e4bdcaa739632265164cd
Source dataset
uspto-grants-2003_09
Patent number
US06624309B1

Reaction notes

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