Toluene → N-(1-phenylcyclohexyl)trimethylacetamide

HRID 2287247Notes

Reaction equation

HRID 2287247 reaction equation
C1(C)C=CC=CC=1.[C:8]1([C:14]2([NH2:20])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH3:21][C:22]([CH3:27])([CH3:26])[C:23](Cl)=[O:24]>N1C=CC=CC=1>[C:8]1([C:14]2([NH:20][C:23](=[O:24])[C:22]([CH3:27])([CH3:26])[CH3:21])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 318621-PhenylcyclohexylamineHCID 62493Pivaloyl chloride

Product 1

HCID 12879909N-(1-phenylcyclohexyl)trimethylacetamideYield 63.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Into a 200 ml four-necked flask, there were charged toluene (150 ml), 1-phenylcyclohexylamine (10.5 g) and pyridine (5.2 g), and trimethylacetyl chloride (7.2 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 pyridine hydrochloride. The toluene layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was recrystallized from ethanol to give 9.8 g of N-(1-phenylcyclohexyl)trimethylacetamide. M.P., 129°-130.5° 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 pyridine hydrochloride
  6. dry with materialThe toluene 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-409925d5de8540908842b44436f77fdb
Source dataset
uspto-grants-1981_05
Patent number
US04270002

Reaction notes

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