Methyl Isobutyl Ketone → HCID 12879907, compound

HRID 2287245Notes

Reaction equation

HRID 2287245 reaction equation
CC(CC(C)C)=O.[C:8]1([C:14]2([NH2:19])[CH2:18][CH2:17][CH2:16][CH2:15]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(N(CC)CC)C.[CH3:27][C:28]([CH3:33])([CH3:32])[C:29](Cl)=[O:30]>O>[C:8]1([C:14]2([NH:19][C:29](=[O:30])[C:28]([CH3:33])([CH3:32])[CH3:27])[CH2:18][CH2:17][CH2:16][CH2:15]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 7909Methyl Isobutyl KetoneHCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 1676511-Phenylcyclopentylamine

Product 1

HCID 12879907HCID 12879907, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a 500 ml four-necked flask, there were charged methylisobutylketone (150 ml), 1-phenylcyclopentylamine (24.3 g) and triethylamine (16.0 g), and trimethylacetyl chloride (18.0 g) was dropwise added thereto while stirring at room temperature. Stirring was continued for 3 hours. After completion of the reaction, water (200 ml) was added thereto and the reaction mixture was gradually heated to remove methylisobutylketone, followed by cooling at room temperature. The precipitated crystals were filtered, washed with water, dried and recrystallized from ethanol to give N-(1-phenylcyclopentyl)trimethylacetamide (33.4 g).

Workup

  1. additionwas dropwise added
  2. stirringStirring
  3. additionwas added
  4. temperaturethe reaction mixture was gradually heated
  5. customto remove methylisobutylketone
  6. temperatureby cooling at room temperature
  7. filtrationThe precipitated crystals were filtered
  8. washwashed with water
  9. customdried
  10. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-e189e105ce5844e6b76dc1e52a2415ca
Source dataset
uspto-grants-1981_05
Patent number
US04270002

Reaction notes

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