Acetic Anhydride → N-ethyl-N-[1-methyl-2-(1-phenyl-2,5-cyclohexadien-1-yl)ethyl]-acetamide

HRID 2287131Notes

Reaction equation

HRID 2287131 reaction equation
[CH3:1][CH:2]([NH:16][CH2:17][CH3:18])[CH2:3][C:4]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:9]=[CH:8][CH2:7][CH:6]=[CH:5]1.[C:19](OC(=O)C)(=[O:21])[CH3:20].C(=O)(O)[O-].[K+]>N1C=CC=CC=1>[CH2:17]([N:16]([CH:2]([CH3:1])[CH2:3][C:4]1([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:5]=[CH:6][CH2:7][CH:8]=[CH:9]1)[C:19](=[O:21])[CH3:20])[CH3:18]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 516893Potassium BicarbonateHCID 23459459alpha-methyl-N-ethyl-1-phenyl-2,5-cyclohexadien-1-ethylamine

Product 1

HCID 23459464N-ethyl-N-[1-methyl-2-(1-phenyl-2,5-cyclohexadien-1-yl)ethyl]-acetamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1.5 g. of α-methyl-N-ethyl-1-phenyl-2,5-cyclohexadien-1-ethylamine are dissolved in a mixture of 10 ml. of acetic acid anhydride and 8 ml. of pyridine and left to stand at room temperature overnight. Then, the mixture is stirred for 2 hours with 2 N aqueous potassium bicarbonate solution and subsequently extracted with ether. The ether phase is washed with dilute aqueous hydrochloride acid and then with water, dried with sodium sulfate, filtered and concentrated to dryness. The crude product obtained is chromatographed on silica gel with ether. There is obtained N-ethyl-N-[1-methyl-2-(1-phenyl-2,5-cyclohexadien-1-yl)ethyl]-acetamide in the form of an oily product.

Workup

  1. extractionsubsequently extracted with ether
  2. washThe ether phase is washed with dilute aqueous hydrochloride acid
  3. dry with materialwith water, dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customThe crude product obtained
  7. customis chromatographed on silica gel with ether

Sources & evidence

ORD record
ord-da647925251d4c3babb3fa97faf4f2e9
Source dataset
uspto-grants-1981_05
Patent number
US04269788

Reaction notes

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