Ethanol → HCID 68145452, compound

HRID 1580131Notes

Reaction equation

HRID 1580131 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]23[CH2:17][CH:13]([NH:14][C:15]2=[O:16])[C:12](=O)[CH2:11][CH2:10]3)[CH:6]=[CH:7][CH:8]=1.O.[NH2:20][NH2:21].C(O)C>C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]23[CH2:17][CH:13]([NH:14][C:15]2=[O:16])[C:12](=[N:20][NH2:21])[CH2:11][CH2:10]3)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 12286596HCID 12286596, compound

Product 1

HCID 68145452HCID 68145452, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 21.73 g of 1-(3-methoxyphenyl)-6-azabicyclo[3,2,1]octane-4,7-dione, 4.9 g of hydrazine hydrate and 170 ml of ethanol is refluxed for 1 hour. After cooling, the mixture is evaporated under reduced pressure to remove solvent. The residue thus obtained is dispersed in benzene and then filtered to give 21.64 g of 1-(3-methoxyphenyl)-6-azabicyclo[3,2,1]octane-4,7-dione-4-hydrazone as crude crystals. A mixture of 21.64 g of 1-(3-methoxyphenyl)-6-azabicyclo[3,2,1]octane-4,7-dione-4-hydrazone, 17.1 g of potassium tert.-butoxide and 400 ml of toluene is refluxed for 2 hours under heating. After cooling, water is added to the mixture, and the aqueous mixture is extracted with ether. The ether extract is washed with water, dried and then evaporated to remove solvent. The residue thus obtained is recrystallized from a mixture of ethylacetate and n-hexane. 17.54 g of 1-(3-methoxyphenyl)-6-azabicyclo[3,2,1]octane-7-one are obtained. M.p. 109° - 111°C.

Workup

  1. temperatureis refluxed for 1 hour
  2. temperatureAfter cooling
  3. customthe mixture is evaporated under reduced pressure
  4. customto remove solvent
  5. customThe residue thus obtained
  6. filtrationfiltered

Sources & evidence

ORD record
ord-d5b978bdb5e54dec90fbc83440b54dc4
Source dataset
uspto-grants-1976_01
Patent number
US03932429

Reaction notes

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