1-(4-Nitrophenyl)-5-phenyl-3-n-propyl-3-azabicyclo[3.1.1]heptane-2,4-dione → 1-(4-Aminophenyl)-5-phenyl-3-n-propyl-3-azabicyclo[3.1.1]heptane-2,4-dione

HRID 35083

Reaction equation

HRID 35083 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]23[CH2:16][C:14]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)([CH2:15]2)[C:13](=[O:23])[N:12]([CH2:24][CH2:25][CH3:26])[C:11]3=[O:27])=[CH:6][CH:5]=1)([O-])=O.CCCCCC.CCOCC>C(OCC)(=O)C.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([C:10]23[CH2:15][C:14]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)([CH2:16]2)[C:13](=[O:23])[N:12]([CH2:24][CH2:25][CH3:26])[C:11]3=[O:27])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 200278081-(4-Nitrophenyl)-5-phenyl-3-n-propyl-3-azabicyclo[3.1.1]heptane-2,4-dioneHCID 21584099Diethylether hexane

Product 1

HCID 200278421-(4-Aminophenyl)-5-phenyl-3-n-propyl-3-azabicyclo[3.1.1]heptane-2,4-dione

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

In a manner analogous to that described in Example 12a, 1.8 g of 1-(4-nitrophenyl)-5-phenyl-3-n-propyl-3-azabicyclo[3.1.1]heptane-2,4-dione are dissolved in 40 ml of ethyl acetate, hydrogenated in the presence of 0.2 g of 5% palladium-on-carbon and worked up. Melting point 144°-145° (from n-hexane/ether).

Sources & evidence

ORD record
ord-b4153e745c30420c892ee1a30fabf655
Source dataset
uspto-grants-1988_08
Patent number
US04764640

Linked notes

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