1-(1-(5-Methoxy-2-methyl-4-nitrophenyl)piperidin-4-yl)-4-methylpiperazine → 2-Methoxy-5-methyl-4-(4-(4-methylpiperazin-1-yl)piperidin-1-yl)aniline

HRID 1256010Notes

Reaction equation

HRID 1256010 reaction equation
[CH3:1][O:2][C:3]1[C:4]([N+:23]([O-])=O)=[CH:5][C:6]([CH3:22])=[C:7]([N:9]2[CH2:14][CH2:13][CH:12]([N:15]3[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]3)[CH2:11][CH2:10]2)[CH:8]=1>[Pd].CO>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N:9]2[CH2:14][CH2:13][CH:12]([N:15]3[CH2:16][CH2:17][N:18]([CH3:21])[CH2:19][CH2:20]3)[CH2:11][CH2:10]2)[C:6]([CH3:22])=[CH:5][C:4]=1[NH2:23]

Participants

4

Reactant 1

HCID 580714941-(1-(5-Methoxy-2-methyl-4-nitrophenyl)piperidin-4-yl)-4-methylpiperazine2×

Product 1

HCID 580714632-Methoxy-5-methyl-4-(4-(4-methylpiperazin-1-yl)piperidin-1-yl)aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Palladium on carbon (10% Degussa Type) (100 mg, 0.94 mmol) was added to a stirring solution of 1-(1-(5-methoxy-2-methyl-4-nitrophenyl)piperidin-4-yl)-4-methylpiperazine (INTERMEDIATE 12, 697 mg, 2.00 mmol) in methanol (10 mL). The reaction mixture was then stirred under hydrogen (1 atm) at RT for 15 h. The reaction mixture was filtered through Celite® and the filtrate was concentrated in vacuo to give the title product which was used in the next step without further purification (566 mg, 66.1%). m/z 319.

Workup

  1. filtrationThe reaction mixture was filtered through Celite®
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-414704d40719464daf0f1a339daa4a5d
Source dataset
uspto-grants-2013_06
Patent number
US08461170B2

Reaction notes

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