Racemic-1-(2-fluoro-4-nitrophenyl)-trans-2,4,5-trimethylpiperazine → Racemic-trans-[1,2,5-trimethyl-4-(4-nitrophenyl)piperazine]

HRID 1011253Notes

Reaction equation

HRID 1011253 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]1[CH3:19].C[C@H]1CN[C@H](C)CN1C1C=CC([N+]([O-])=O)=CC=1>>[CH3:18][N:14]1[CH2:13][C@@H:12]([CH3:19])[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 57664351Racemic-1-(2-fluoro-4-nitrophenyl)-trans-2,4,5-trimethylpiperazineHCID 57664370(2S,5R)-2,5-Dimethyl-1-(4-nitrophenyl)piperazine

Product 1

HCID 131729017Racemic-trans-[1,2,5-trimethyl-4-(4-nitrophenyl)piperazine]Yield 111%

Procedure

Crude racemic-trans-[1,2,5-trimethyl-4-(4-nitrophenyl)piperazine] (7.48 g, 111% 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 racemic-[trans-2,5-dimethyl-1-(4-nitrophenyl)-piperazine] (6.34 g, 25.0 mmol). LCMS-ESI (m/z): calcd for C13H19N3O2, 249; [M+H]+ found, 250.

Sources & evidence

ORD record
ord-d751e06db7b546bba27dbd8a44392bb0
Source dataset
uspto-grants-2011_07
Patent number
US07977352B2

Reaction notes

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