p-Fluoronitrobenzene → cis-3,5-Dimethyl-1-(4-nitrophenyl)piperazine

HRID 1011248Notes

Reaction equation

HRID 1011248 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])[NH:14][CH2:13][C@@H:12]1C.F[C:20]1C=CC([N+]([O-])=O)=CC=1.C[C@H]1CNC[C@@H](C)N1>>[CH3:17][C@H:15]1[NH:14][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]1

Participants

4

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 6950261rel-(2R,6S)-2,6-dimethylpiperazineHCID 57664344Racemic-1-(2-fluoro-4-nitrophenyl)-trans-2,5-dimethylpiperazine

Product 1

HCID 7059963cis-3,5-Dimethyl-1-(4-nitrophenyl)piperazineYield 95%

Procedure

Crude cis-3,5-Dimethyl-1-(4-nitrophenyl)piperazine (4.91 g, 95% recovery) is prepared according to the method described above for the synthesis of racemic-1-(2-fluoro-4-nitrophenyl)-trans-2,5-dimethylpiperazine by treatment of 1-fluoro-4-nitrobenzene (3.08 g, 21.8 mmol) with cis-2,6-dimethylpiperazine (2.50 g, 21.8 mmol). The crude product is used in the next step without chromatographic purification. LCMS-ESI (m/z): calcd for C12H17N3O2, 235; [M+H]+ found, 236.

Workup

  1. customThe crude product is used in the next step without chromatographic purification

Sources & evidence

ORD record
ord-dcb79cfffd694d5b81d9d2619a842aa9
Source dataset
uspto-grants-2011_07
Patent number
US07977352B2

Reaction notes

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