Methyl iodide → HCID 12286607, compound

HRID 1580133Notes

Reaction equation

HRID 1580133 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([C:11]23[CH2:19][CH:15]([NH:16][C:17]2=[O:18])[CH2:14][CH2:13][CH2:12]3)[CH:8]=[CH:9][CH:10]=1.[CH3:20]I>CS(C)=O>[CH3:3][O:4][C:5]1[CH:6]=[C:7]([C:11]23[CH2:19][CH:15]([N:16]([CH3:20])[C:17]2=[O:18])[CH2:14][CH2:13][CH2:12]3)[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 12286599HCID 12286599, compound

Product 1

HCID 12286607HCID 12286607, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
70 °C

Procedure

0.36 g of 69% sodium hydride is added to 40 ml of dimethylsulfoxide, The mixture is heated at 70°C for 30 minutes in a nitrogen atmosphere. 2 g of 1-(3-methoxyphenyl)-6-azabicyclo[3,2,1]octane-7-one are added to the mixture at 10° to 15°C. Then, the mixture is stirred at room temperature for 1 hour. 2.1 G of methyl iodide are added to the mixture, and the mixture is further stirred at room temperature for 2 hours. The reaction mixture is poured into ice-water and extracted with ether. The ether extract is washed with water, dried and then evaporated to remove solvent. The residue thus obtained is recrystallized from n-hexane. 2 g of 1-(3-methoxyphenyl)-6-methyl-6-azabicyclo[3,2,1]octane-7-one are obtained. M.p. 68° - 70°C.

Workup

  1. stirringthe mixture is further stirred at room temperature for 2 hours
  2. extractionextracted with ether
  3. extractionThe ether extract
  4. washis washed with water
  5. customdried
  6. customevaporated
  7. customto remove solvent
  8. customThe residue thus obtained
  9. customis recrystallized from n-hexane

Sources & evidence

ORD record
ord-fe19a77b2dcc4b53b022e4bb447bd273
Source dataset
uspto-grants-1976_01
Patent number
US03932429

Reaction notes

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