cis-3,5-Dimethyl-1-(4-nitrophenyl)piperazine → cis-1,2,6-Trimethyl-4-(4-nitrophenyl)piperazine

HRID 1011252Notes

Reaction equation

HRID 1011252 reaction equation
F[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]1[CH2:16][C@@H:15]([CH3:17])[N:14]([CH3:18])[CH2:13][C@@H:12]1C.[CH3:20][C@H]1N[C@@H](C)CN(C2C=CC([N+]([O-])=O)=CC=2)C1>>[CH3:18][N:14]1[C@H:13]([CH3:20])[CH2:12][N:11]([C:3]2[CH:2]=[CH:7][C:6]([N+:8]([O-:10])=[O:9])=[CH:5][CH:4]=2)[CH2:16][C@@H:15]1[CH3:17]

Participants

3

Reactant 2

HCID 7059963cis-3,5-Dimethyl-1-(4-nitrophenyl)piperazineHCID 57664351Racemic-1-(2-fluoro-4-nitrophenyl)-trans-2,4,5-trimethylpiperazine

Product 1

HCID 57664389cis-1,2,6-Trimethyl-4-(4-nitrophenyl)piperazineYield 106%

Procedure

Crude cis-1,2,6-trimethyl-4-(4-nitrophenyl)piperazine (5.55 g, 106% recovery) is prepared according to the method described above for the synthesis of racemic-1-(2-fluoro-4-nitrophenyl)-trans-2,4,5-trimethylpiperazine from cis-3,5-Dimethyl-1-(4-nitrophenyl)piperazine (4.91 g, 20.8 mmol). LCMS-ESI (m/z): calcd for C13H19N3O2, 249; [M+H]+ found, 250.

Sources & evidence

ORD record
ord-f313cfa70977415093109683e3c35d45
Source dataset
uspto-grants-2011_07
Patent number
US07977352B2

Reaction notes

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