Benzene → HCID 12879908, compound

HRID 2287246Notes

Reaction equation

HRID 2287246 reaction equation
C1C=CC=CC=1.[CH3:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2([NH2:19])[CH2:18][CH2:17][CH2:16][CH2:15]2)=[CH:10][CH:9]=1.[CH3:20][C:21]([CH3:26])([CH3:25])[C:22](Cl)=[O:23]>C(N(CC)CC)C>[CH3:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2([NH:19][C:22](=[O:23])[C:21]([CH3:26])([CH3:25])[CH3:20])[CH2:18][CH2:17][CH2:16][CH2:15]2)=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 241BenzeneHCID 62493Pivaloyl chlorideHCID 234601061-p-Tolyl-cyclopentylamine

Product 1

HCID 12879908HCID 12879908, compoundYield 83.7%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Into a 200 ml four-necked flask, there were charged benzene (100 ml), 1-(p-methylphenyl)cyclopentylamine (8.8 g) and triethylamine (6.1 g), and trimethylacetyl chloride (6.0 g) was dropwise added thereto while stirring at room temperature. Stirring was continued for 3 hours. After completion of the reaction, the reaction mixture was washed with water to remove triethylamine hydrochloride. After the benzene layer was dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The residue was recrystallized from ethanol to give 10.8 g of N-[1-(p-methylphenyl)cyclopentyl]trimethylacetamide. M.P., 166°-167° C.

Workup

  1. additionwas dropwise added
  2. stirringStirring
  3. customAfter completion of the reaction
  4. washthe reaction mixture was washed with water
  5. customto remove triethylamine hydrochloride
  6. dry with materialAfter the benzene layer was dried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-65ca2764b18840929a114c2a547ff7bc
Source dataset
uspto-grants-1981_05
Patent number
US04270002

Reaction notes

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