2-Azabicyclo(2.2.1)hept-5-en-3-one → 2-{4-[4-(2,4-Dimethylphenyl)piperazine-1-carbonyl]phenyl}-2-azabicyclo[2.2.1]hept-5-en-3-one

HRID 2411731Notes

Reaction equation

HRID 2411731 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][C:17]=3[CH3:23])[CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1.[CH:24]12[CH2:30][CH:27]([CH:28]=[CH:29]1)[C:26](=[O:31])[NH:25]2>>[CH3:23][C:17]1[CH:18]=[C:19]([CH3:22])[CH:20]=[CH:21][C:16]=1[N:13]1[CH2:14][CH2:15][N:10]([C:8]([C:5]2[CH:6]=[CH:7][C:2]([N:25]3[C:26](=[O:31])[CH:27]4[CH2:30][CH:24]3[CH:29]=[CH:28]4)=[CH:3][CH:4]=2)=[O:9])[CH2:11][CH2:12]1

Participants

3

Reactant 2

HCID 5486782-Azabicyclo(2.2.1)hept-5-en-3-oneHCID 58484623(4-Bromophenyl)[4-(2,4-dimethylphenyl)piperazin-1-yl]methanone

Product 1

HCID 712519762-{4-[4-(2,4-Dimethylphenyl)piperazine-1-carbonyl]phenyl}-2-azabicyclo[2.2.1]hept-5-en-3-oneYield 15.1%

Procedure

Using (4-bromophenyl)[4-(2,4-dimethylphenyl)piperazin-1-yl]methanone (747 mg) described in Preparation Example 170 and 2-azabicyclo[2.2.1]hept-5-en-3-one (218 mg) and by the reaction and treatment in the same manner as in Example 1, the title compound (121 mg) was obtained.

Sources & evidence

ORD record
ord-627250b91ad1431badb1f34ed599255e
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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