Water → HCID 13590890, compound

HRID 247618Notes

Reaction equation

HRID 247618 reaction equation
[H-].[Na+].[CH:3]1([NH:10][C:11](=[O:13])[CH3:12])[CH2:9][CH2:8][CH2:7][CH2:6][CH:5]=[CH:4]1.[CH3:14]I.O>CN(C=O)C>[CH3:14][N:10]([CH:3]1[CH2:9][CH2:8][CH2:7][CH2:6][CH:5]=[CH:4]1)[C:11](=[O:13])[CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 12677648HCID 12677648, compound

Product 1

HCID 13590890HCID 13590890, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension (10 ml) of sodium hydride (0.24 g, 10 mmoles) in DMF was added N-(2-cycloheptenyl)acetamide (1.53 g, 10 mmoles) in DMF (1 ml) at 0° C. After completion of the addition, the temperature of the mixture was raised to room temperature, and after stirring for 15 minutes, methyl iodide (2.84 g, 20 mmoles) was added dropwise. The resulting mixture was stirred at room temperature for 24 hours, poured into water (20 ml) and extracted with ether. The oily product obtained by concentration was purified by chromatography on silica gel to obtain 0.84 g of N-methyl-N-(2-cycloheptenyl)acetamide [Compound (55)].

Workup

  1. additionAfter completion of the addition
  2. stirringThe resulting mixture was stirred at room temperature for 24 hours
  3. extractionextracted with ether
  4. customThe oily product obtained by concentration
  5. customwas purified by chromatography on silica gel

Sources & evidence

ORD record
ord-a2cee2ddc711455a8a9948bff1cbbb2f
Source dataset
uspto-grants-1987_11
Patent number
US04709052

Reaction notes

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