1-Methyl-4-(4-methyl-3-nitrophenyl)piperazine → 2-Methyl-5-(4-methylpiperazin-1-yl)benzenamine

HRID 1907441Notes

Reaction equation

[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([N+:15]([O-])=O)[CH:9]=2)[CH2:4][CH2:3]1>C(O)C.C1CCCCC=1.[Pd]>[CH3:14][C:11]1[CH:12]=[CH:13][C:8]([N:5]2[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]2)=[CH:9][C:10]=1[NH2:15]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 1-methyl-4-(4-methyl-3-nitro-phenyl)-piperazine (9.0 g, 38.29 mmol) in ethanol (100 mL) and cyclohexene (7 ml), Pd/C 10% (1.5 g) was added. The mixture was heated at 80° C. for 6 hours until HPLC revealed the disappearance of the starting material. The Pd was filtered from the reaction and the solvents were removed from the filtrate under reduced pressure. The crude was diluted with DCM and treated with HCl in dioxane; the precipitate was collected and washed with diethyl ether to give the final compound as a brown solid in quantitative yield.

Workup

filtrationThe Pd was filtered from the reaction
customthe solvents were removed from the filtrate under reduced pressure
additionThe crude was diluted with DCM
additiontreated with HCl in dioxane
customthe precipitate was collected
washwashed with diethyl ether

Sources & evidence

ORD record: ord-8ae15f576e02456c82c4b28391496808
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598172B2

Reaction notes

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