cis-4-(2-Fluoro-4-nitrophenyl)-1,2,6-trimethylpiperazine → 3-Fluoro-4-(cis-3,4,5-trimethyl-piperazin-1-yl)-phenylamine

HRID 1011257Notes

Reaction equation

HRID 1011257 reaction equation
C[C@H]1CN(C)[C@H](C)CN1C1C=CC(N)=CC=1.[F:17][C:18]1[CH:23]=[C:22]([N+:24]([O-])=O)[CH:21]=[CH:20][C:19]=1[N:27]1[CH2:32][C@@H:31]([CH3:33])[N:30]([CH3:34])[C@@H:29]([CH3:35])[CH2:28]1>[Pd]>[F:17][C:18]1[CH:23]=[C:22]([NH2:24])[CH:21]=[CH:20][C:19]=1[N:27]1[CH2:32][C@H:31]([CH3:33])[N:30]([CH3:34])[C@H:29]([CH3:35])[CH2:28]1

Participants

4

Reactant 2

HCID 57664380cis-4-(2-Fluoro-4-nitrophenyl)-1,2,6-trimethylpiperazineHCID 66888039Racemic 4-(trans-2,4,5-trimethyl-piperazin-1-yl)-phenylamine

Product 1

HCID 576643883-Fluoro-4-(cis-3,4,5-trimethyl-piperazin-1-yl)-phenylamineYield 84.3%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Using the method described above for the synthesis of racemic-4-(trans-2,4,5-Trimethyl-piperazin-1-yl)-phenylamine, treatment of cis-4-(2-fluoro-4-nitrophenyl)-1,2,6-trimethylpiperazine (1.39 g, 5.20 mmol) with H2 and 10% Pd/C (120 mg) provided crude 3-fluoro-4-(cis-3,4,5-trimethyl-piperazin-1-yl)-phenylamine (1.04 g, 84% recovery, 96% purity as determined by LC/MS analysis @ UV 254 nm detection,). The crude product is used in the next step without further purification. LCMS-ESI (m/z): calcd for C13H20FN3, 237; [M+H]+ found, 238.

Sources & evidence

ORD record
ord-e05c6f4ce9b2468292ebe25060c1c602
Source dataset
uspto-grants-2011_07
Patent number
US07977352B2

Reaction notes

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