Dimethylformamide → p-Cyclopropanoyl N,N,N-Trimethylanilinium Iodide

HRID 483294Notes

Reaction equation

HRID 483294 reaction equation
[CH:1]1([C:4]([C:6]2[CH:11]=[CH:10][C:9]([N:12]([CH3:14])[CH3:13])=[CH:8][CH:7]=2)=[O:5])[CH2:3][CH2:2]1.[CH3:15]N(C)C=O.C[I:21]>C(OCC)(=O)C>[I-:21].[CH:1]1([C:4]([C:6]2[CH:7]=[CH:8][C:9]([N+:12]([CH3:15])([CH3:14])[CH3:13])=[CH:10][CH:11]=2)=[O:5])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 14924451HCID 14924451, compound

Product 1

HCID 19751949p-Cyclopropanoyl N,N,N-Trimethylanilinium IodideYield 17.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

p-N,N-Dimethylaminophenyl cyclopropyl ketone (186.50 mg, 0.99 mmol) is added to 2 ml of dimethylformamide (DMF). Methyl iodide (0.24 g, 7.4 mmol) is added to the solution, the flask stoppered and the solution stirred for 18 hrs. Ethyl acetate is added to the flask to precipitate the product and the solution is filtered. The precipitate is washed with ethyl acetate, ether and chloroform. The precipitate is then dissolved in a minimal amount of methanol and filtered. Ether is added to the filtrate to precipitate the product. The product is filtered and washed with ether and dried. This yielded 2B as a white crystalline solid (56.25 mg, 17.2% yield); m.p. >280° C.; IR (KBr):1660 cm-1 (C=O): NMR (CD3CN) δ:1.15 (d, 4H); 2.60 (m, 1H ); 3.61 (s, 9H); 7.93 (d, 2H); 8.24 (d, 2H); mass spectrum m/e=189 (M-CH3I). Calculated for C13H18ION:C, 47.14; H, 5.49; I, 38.31, N, 4.23. Found: C, 45.60; H, 5.49; I 38.91; N, 4.50. HPLC analysis of the product show that no cyclopropyl p-fluorophenyl ketone is present in the final product.

Workup

  1. customto precipitate the product
  2. filtrationthe solution is filtered
  3. washThe precipitate is washed with ethyl acetate, ether and chloroform
  4. dissolutionThe precipitate is then dissolved in a minimal amount of methanol
  5. filtrationfiltered
  6. additionEther is added to the filtrate
  7. customto precipitate the product
  8. filtrationThe product is filtered
  9. washwashed with ether
  10. customdried

Sources & evidence

ORD record
ord-2fbbe7e44c6847cea1a62c316ce0b4e1
Source dataset
uspto-grants-1993_07
Patent number
USH0001209

Reaction notes

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