1,5-Di-(4-nitrophenyl)-3-n-propyl-3-azabicyclo[3.1.1]heptane-2,4-dione → 1,5-Di-(4-aminophenyl)-3-n-propyl-3-azabicyclo[3.1.1]heptane-2,4-dione

HRID 35084Notes

Reaction equation

HRID 35084 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][C:20]([N+:23]([O-])=O)=[CH:19][CH:18]=4)([CH2:15]2)[C:13](=[O:26])[N:12]([CH2:27][CH2:28][CH3:29])[C:11]3=[O:30])=[CH:6][CH:5]=1)([O-])=O.CCOCC.C(Cl)Cl>C(OCC)(=O)C.[Pd]>[NH2:23][C:20]1[CH:19]=[CH:18][C:17]([C:14]23[CH2:16][C:10]([C:7]4[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=4)([CH2:15]2)[C:11](=[O:30])[N:12]([CH2:27][CH2:28][CH3:29])[C:13]3=[O:26])=[CH:22][CH:21]=1

Participants

5

Reactant 2

HCID 148726211,5-Di-(4-nitrophenyl)-3-n-propyl-3-azabicyclo[3.1.1]heptane-2,4-dioneHCID 21881112Ethyl ether methylene chloride

Product 1

HCID 200278201,5-Di-(4-aminophenyl)-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, 0.4 g of 1,5-di-(4-nitrophenyl)-3-n-propyl-3-azabicyclo[3.1.1]heptane-2,4-dione are dissolved in 15 ml of ethyl acetate, hydrogenated in the presence of 80 mg of 5% palladium-on-carbon and worked up. Melting point 149°-150° (from ether/methylene chloride).

Sources & evidence

ORD record
ord-8912190ed3464e4091fb6280002f0b9a
Source dataset
uspto-grants-1988_08
Patent number
US04764640

Reaction notes

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