Racemic-1-(2-fluoro-4-nitrophenyl)-trans-2,4,5-trimethylpiperazine → cis-4-(2-Fluoro-4-nitrophenyl)-1,2,6-trimethylpiperazine

HRID 1011254Notes

Reaction equation

HRID 1011254 reaction equation
[F:1][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.F[C:21]1C=C([N+]([O-])=O)C=CC=1N1C[C@H](C)N[C@H](C)C1>>[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]1[CH2:12][C@@H:13]([CH3:21])[N:14]([CH3:18])[C@@H:15]([CH3:17])[CH2:16]1

Participants

3

Reactant 2

HCID 57664351Racemic-1-(2-fluoro-4-nitrophenyl)-trans-2,4,5-trimethylpiperazineHCID 57664386(3R,5S)-1-(2-Fluoro-4-nitrophenyl)-3,5-dimethylpiperazine

Product 1

HCID 57664380cis-4-(2-Fluoro-4-nitrophenyl)-1,2,6-trimethylpiperazineYield 100%

Procedure

Crude cis-4-(2-Fluoro-4-nitrophenyl)-1,2,6-trimethylpiperazine (6.1 g, 100% 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 1-(2-fluoro-4-nitrophenyl)-cis-3,5-dimethylpiperazine (5.71 g, 24.2 mmol). LCMS-ESI (m/z): calcd for C13HBFN3O2, 267; [M+H]+ found, 268.

Sources & evidence

ORD record
ord-ecbe40f27deb42c990cd04e8cda1e2df
Source dataset
uspto-grants-2011_07
Patent number
US07977352B2

Reaction notes

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