HCID 14872615, compound → 1-(4-Amino-phenyl)-3-propyl-3-aza-bicyclo[3.1.1]heptane-2,4-dione

HRID 1722844Notes

Reaction equation

HRID 1722844 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]23[CH2:16][CH:14]([CH2:15]2)[C:13](=[O:17])[N:12]([CH2:18][CH2:19][CH3:20])[C:11]3=[O:21])=[CH:6][CH:5]=1)([O-])=O.[H][H]>[Pd].C(OCC)(=O)C>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]23[CH2:15][CH:14]([CH2:16]2)[C:13](=[O:17])[N:12]([CH2:18][CH2:19][CH3:20])[C:11]3=[O:21])=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 14872615HCID 14872615, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 148726221-(4-Amino-phenyl)-3-propyl-3-aza-bicyclo[3.1.1]heptane-2,4-dione

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

0.35 g of 5% palladium-on-carbon catalyst is added to a solution of 3.5 g of 1-(4-nitrophenyl)-3-n-propyl-3-azabicyclo[3.1.1]heptane-2,4-dione in 70 ml of ethyl acetate and the whole is hydrogenated under normal pressure and at 30°-35° in a hydrogen atmosphere. When the absorption of hydrogen is complete, the reaction mixture is diluted with 30 ml of methylene chloride and freed of catalyst by filtration over HYFLO Super-Cel ®. The solvent is evaporated off in vacuo, and the residue is recrystallised from a mixture of ethyl acetate/n-hexane, yielding the title compound in the form of white crystals having a melting point of 166-167°.

Workup

  1. customWhen the absorption of hydrogen
  2. additionthe reaction mixture is diluted with 30 ml of methylene chloride
  3. filtrationfreed of catalyst by filtration over HYFLO Super-Cel ®
  4. customThe solvent is evaporated off in vacuo
  5. customthe residue is recrystallised from a mixture of ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-1682d040ee85471097ddac27ca711ab6
Source dataset
uspto-grants-1989_08
Patent number
US04857660

Reaction notes

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