Ethyl Acetate → 2-Methoxy-4-(4-(4-methylpiperazin-1-yl)piperidin-1-yl)aniline

HRID 1261966Notes

Reaction equation

HRID 1261966 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:17][CH2:16][CH:15]([N:18]3[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]3)[CH2:14][CH2:13]2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-])=O.C(OCC)(=O)C>[Pd].CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:17][CH2:16][CH:15]([N:18]3[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]3)[CH2:14][CH2:13]2)[CH:6]=[CH:7][C:8]=1[NH2:9]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 567772491-(1-(3-Methoxy-4-nitrophenyl)piperidin-4-yl)-4-methylpiperazine

Product 1

HCID 457899912-Methoxy-4-(4-(4-methylpiperazin-1-yl)piperidin-1-yl)aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a Paar bottle (250 mL) was added 10% Palladium on Carbon (50% Wet) followed by a solution of 1-[1-(3-Methoxy-4-nitro-phenyl)-piperidin-4-yl]-4-methyl-piperazine (0.90 g, 0.0027 mol) in 2:1 Ethyl acetate:Methanol (100 mL). The mixture was degassed and charged with Hydrogen (50 psi). The reaction was shaken until equilibrium had been reached. A total of 25 psi of Hydrogen was adsorbed. The mixture was degassed and kept under an atmosphere of Nitrogen. The suspension was filtered through a plug of diatomaceous earth and rinsed with dichloromethane. The filtrate was evaporated to yield a light purple solid 2-Methoxy-4-[4-(4-methyl-piperazin-1-yl)-piperidin-1-yl]-phenylamine. (0.82 g). mp=94-99° C. 1H NMR (400 MHz, CDCl3, δ, ppm): 6.63 (d, 1H, J=8.3 Hz), 6.52 (d, 1H, J=1.5 Hz), 6.44-6.39 (m, 1H), 3.83 (s, 3H), 3.75-3.25 (m, 4H), 2.80-2.25 (m, 14H), 1.96-1.87 (m, 2H), 1.78-1.65 (m, 2H). LC/MS=305.16 (MH)+

Workup

  1. customThe mixture was degassed
  2. additioncharged with Hydrogen (50 psi)
  3. customThe mixture was degassed
  4. filtrationThe suspension was filtered through a plug of diatomaceous earth
  5. washrinsed with dichloromethane
  6. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-33f226dbc447419694123739e45a2657
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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