Water → HCID 21564945, compound

HRID 1580136Notes

Reaction equation

HRID 1580136 reaction equation
[Li].[CH3:2]I.[CH3:4][O:5][C:6]1[CH:7]=[C:8]([C:12]23[CH2:21][CH:16]([N:17]([CH3:20])[C:18]2=O)[CH2:15][CH2:14][CH2:13]3)[CH:9]=[CH:10][CH:11]=1.O>CCOCC.C1C=CC=CC=1>[CH3:4][O:5][C:6]1[CH:7]=[C:8]([C:12]23[CH2:21][CH:16]([N:17]([CH3:20])[C:18]2=[CH2:2])[CH2:15][CH2:14][CH2:13]3)[CH:9]=[CH:10][CH:11]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 3028194LithiumHCID 12286607HCID 12286607, compound

Product 1

HCID 21564945HCID 21564945, compoundYield 100.8%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent2×

Procedure

0.17 g of lithium is added to 8 ml of absolute ether in a nitrogen atmosphere, and a solution of 1.6 g of methyl iodide in 3 ml of absolute ether is added dropwise thereto at 0° to -5°C. The mixture is stirred at the same temperature for 30 minutes. Then, a solution of 1.0 g of 1-(3-methoxyphenyl)-6-methyl-6-azabicyclo[3,2,1]octane-7-one in 30 ml of benzene is added dropwise to the mixture at room temperature for 5 minutes. The mixture is refluxed for 3 hours. Water is added to the mixture under ice-cooling, and the aqueous mixture is extracted with ether. The ether extract is washed with water, dried and then evaporated to remove solvent, whereby 1.0 g of 1-(3-methoxyphenyl)-6-methyl-7-methylidene-6-azabicyclo[3,2,1]octane is obtained. The product thus obtained is dissolved in 60 ml of ethanol. 300 mg of sodium borohydride are added to the ethanol solution at 10° to 15°C. Then, the mixture is stirred at room temperature for 20 hours. After the reaction, the mixture is concentrated under reduced pressure. Water is added to the residue, and the aqueous mixture is extracted with chloroform. The chloroform extract is washed with water, dried and then evaporated to remove solvent. Methanolic hydrogen bromide is added to the residue in ether, and the crystalline precipitate is collected by filtration. The precipitate is recrystallized from a mixture of ethanol, acetone and ether. 1.1 g of 1-(3-methoxyphenyl)-6,7-dimethyl-6-azabicyclo[3,2,1]octane hydrobromide are obtained. M.p. 175° - 177°C.

Workup

  1. customat 0° to -5°C
  2. temperatureThe mixture is refluxed for 3 hours
  3. temperaturecooling
  4. extractionthe aqueous mixture is extracted with ether
  5. extractionThe ether extract
  6. washis washed with water
  7. customdried
  8. customevaporated
  9. customto remove solvent

Sources & evidence

ORD record
ord-2be4575288ea402d9de3d2f306ef741e
Source dataset
uspto-grants-1976_01
Patent number
US03932429

Reaction notes

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