3-(2-methoxyiminopropyl)-4-(4-methoxyphenyl)-1,5,6,7-tetrahydro-2H-azepinone → HCID 20332954, compound

HRID 26431Notes

Reaction equation

HRID 26431 reaction equation
CO[N:3]=[C:4]([CH3:22])[CH2:5][C:6]1[C:7](=[O:21])[NH:8][CH2:9][CH2:10][CH2:11][C:12]=1[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1.[H][H]>C(O)C.[Ni]>[NH2:3][CH:4]([CH3:22])[CH2:5][C:6]1[C:7](=[O:21])[NH:8][CH2:9][CH2:10][CH2:11][C:12]=1[C:13]1[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 867364713-(2-methoxyiminopropyl)-4-(4-methoxyphenyl)-1,5,6,7-tetrahydro-2H-azepinoneHCID 178418361HCID 178418361, compound

Product 1

HCID 20332954HCID 20332954, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

The solution of 6.5 g of 3-(2-methoxyiminopropyl)-4-(4-methoxyphenyl)-1,5,6,7-tetrahydro-2H-azepinone in 150 ml of ethanol is hydrogenated at room temperature and atmospheric pressure in the presence of 10 g of Raney nickel until the uptake of 2 mole equivalents of hydrogen is complete. The mixture is filtered, the filtrate evaporated and the residue dissolved in 100 ml of water and 10 ml of 6 N hydrochloric acid. The acidic solution is washed with diethyl ether, filtered, basified with 30 ml of 3 N aqueous sodium hydroxide and repeatedly extracted with chloroform. The extract is dried, evaporated and the residue is purified by suspension in diethyl ether, to give the 3-(2-aminopropyl)-4-(4-methoxyphenyl)-1,5,6,7-tetrahydro-2H-azepinone melting at 131°-133°.

Workup

  1. customis hydrogenated at room temperature
  2. filtrationThe mixture is filtered
  3. customthe filtrate evaporated
  4. dissolutionthe residue dissolved in 100 ml of water
  5. washThe acidic solution is washed with diethyl ether
  6. filtrationfiltered
  7. extractionrepeatedly extracted with chloroform
  8. customThe extract is dried
  9. customevaporated
  10. customthe residue is purified by suspension in diethyl ether

Sources & evidence

ORD record
ord-b22b5f316c484a7f9559a49fc4cf3e77
Source dataset
uspto-grants-1979_04
Patent number
US04150129

Reaction notes

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