cis-1,2,6-Trimethyl-4-(4-nitrophenyl)piperazine → 4-(cis-3,4,5-Trimethyl-piperazin-1-yl)-phenylamine

HRID 1011258Notes

Reaction equation

HRID 1011258 reaction equation
C[C@H]1CN(C)[C@H](C)CN1C1C=CC(N)=CC=1.[CH3:17][N:18]1[C@H:23]([CH3:24])[CH2:22][N:21]([C:25]2[CH:30]=[CH:29][C:28]([N+:31]([O-])=O)=[CH:27][CH:26]=2)[CH2:20][C@@H:19]1[CH3:34]>[Pd]>[CH3:34][C@H:19]1[N:18]([CH3:17])[C@@H:23]([CH3:24])[CH2:22][N:21]([C:25]2[CH:26]=[CH:27][C:28]([NH2:31])=[CH:29][CH:30]=2)[CH2:20]1

Participants

4

Reactant 2

HCID 57664389cis-1,2,6-Trimethyl-4-(4-nitrophenyl)piperazineHCID 66888039Racemic 4-(trans-2,4,5-trimethyl-piperazin-1-yl)-phenylamine

Product 1

HCID 576643784-(cis-3,4,5-Trimethyl-piperazin-1-yl)-phenylamineYield 104.9%

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-1,2,6-trimethyl-4-(4-nitrophenyl)piperazine (1.28 g, 5.13 mmol) with H2 and 10% Pd/C (130 mg) provided crude 4-(cis-3,4,5-Trimethyl-piperazin-1-yl)-phenylamine (1.18 g, 101% recovery, >85% purity as determined by LC/MS analysis @ UV 254 nm detection). The crude product was used in the next step without further purification. LCMS-ESI (m/z): calcd for C13H21N3, 219; [M+H]+ found, 220.

Sources & evidence

ORD record
ord-dc1141a6527141fb8e798ed9d77e1e77
Source dataset
uspto-grants-2011_07
Patent number
US07977352B2

Reaction notes

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