Dimethylformamide → HCID 21186440, compound

HRID 1384260Notes

Reaction equation

HRID 1384260 reaction equation
[H-].[Na+].[CH3:3]N(C)C=O.[CH:8]1([CH2:16][N:17]2[CH2:22]C[C:20](=O)[CH2:19][CH2:18]2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.CI.C([O:29][CH2:30][CH3:31])(=O)C>>[CH:8]1([CH2:16][N:17]2[CH2:22][CH:31]([CH3:3])[C:30](=[O:29])[CH:19]([CH3:20])[CH2:18]2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 21186413HCID 21186413, compound

Product 1

HCID 21186440HCID 21186440, compound

Procedure

60% Sodium hydride of 105 mg was added to a dimethylformamide 6 ml solution of 1-cyclooctylmethyl-4-piperidone of 300 mg, and the solution was stirred at a room temperature for 30 minutes. Then, methyl iodide of 160 μl was added thereto, and the solution was further stirred for 8 hours. The reaction solution was diluted with ethyl acetate and washed with water and saturated brine, followed by drying on anhydrous sodium sulfate. Then, the solvent was distilled off, and the resulting residue was separated and refined by means of silica gel column chromatography (ethyl acetate/hexane=1/20), whereby the captioned compound of 45 mg was obtained in the form of colorless liquid. Further, 1-cyclooctylmethyl-3,5-dimethyl-4-piperidone of 42 mg was obtained in the form of colorless liquid.

Workup

  1. stirringthe solution was further stirred for 8 hours
  2. washwashed with water and saturated brine
  3. dry with materialby drying on anhydrous sodium sulfate
  4. distillationThen, the solvent was distilled off
  5. customthe resulting residue was separated
  6. customwas obtained in the form of colorless liquid

Sources & evidence

ORD record
ord-14c0cba7037f4561832c86221196d1a5
Source dataset
uspto-grants-2001_07
Patent number
US06258825B1

Reaction notes

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