Hydrochloric Acid → 2-Methoxy-4-(4-(4-methylpiperazin-1-yl)piperidin-1-yl)aniline

HRID 921337Notes

Reaction equation

HRID 921337 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.Cl>C(O)C.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:17][CH2:16][CH:15]([N:18]3[CH2:19][CH2:20][N:21]([CH3:24])[CH2:22][CH2:23]3)[CH2:14][CH2:13]2)[CH:6]=[CH:7][C:8]=1[NH2:9]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 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)anilineYield 88%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

The a solution of 1-[1-(3-methoxy-4-nitrophenyl)piperidin-4-yl]-4-methylpiperazine (0.3 g, 0.90 mmol) in 10 mL of ethanol purged with argon was added 10% Palladium on carbon (0.060 g). The hydrogenation was finished under 30 psi after 4 h. The mixture was passed through Celite to a flask containing HCl in ethanol. Concentration of the filtrate gave the final product (0.15 g, 88% yield). MS/ES+: m/z=334.

Workup

  1. customThe mixture was passed through Celite to a flask

Sources & evidence

ORD record
ord-7ecc9616c316405d860e4883bba9923e
Source dataset
uspto-grants-2016_03
Patent number
US09273077B2

Reaction notes

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