p-Fluoronitrobenzene → (2S,5R)-2,5-Dimethyl-1-(4-nitrophenyl)piperazine

HRID 1011250Notes

Reaction equation

HRID 1011250 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]1[CH3:18].FC1C=CC([N+]([O-])=O)=CC=1.C[C@H]1CN[C@H](C)CN1>>[CH3:18][C@H:12]1[CH2:13][NH:14][C@H:15]([CH3:17])[CH2:16][N:11]1[C:3]1[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][CH:2]=1

Participants

4

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 2206722,5-Dimethylpiperazine, trans-HCID 57664344Racemic-1-(2-fluoro-4-nitrophenyl)-trans-2,5-dimethylpiperazine

Product 1

HCID 57664370(2S,5R)-2,5-Dimethyl-1-(4-nitrophenyl)piperazineYield 31%

Procedure

Racemic-[trans-2,5-dimethyl-1-(4-nitrophenyl)piperazine] (6.34 g, 31%) 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 (12.3 g, 87.5 mmol) with trans-2,5-dimethylpiperazine (10.0 g, 87.5 mmol). LCMS-ESI (m/z): calcd for C12H17N3O2, [M+H]+235; found, 236.

Sources & evidence

ORD record
ord-a172ba563a3543589bbce44ca5278f36
Source dataset
uspto-grants-2011_07
Patent number
US07977352B2

Reaction notes

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