2-{[4-(1-Methylpiperazin-4-yl)piperidin-1-yl]carbonylamino}-4-(4-nitrophenoxy)pyridine → 4-(4-Aminophenoxy)-2-{[4-(1-methylpiperazin-4-yl)piperidin-1-yl]carbonylamino}pyridine

HRID 492892Notes

Reaction equation

HRID 492892 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH:8]2[CH2:13][CH2:12][N:11]([C:14]([NH:16][C:17]3[CH:22]=[C:21]([O:23][C:24]4[CH:29]=[CH:28][C:27]([N+:30]([O-])=O)=[CH:26][CH:25]=4)[CH:20]=[CH:19][N:18]=3)=[O:15])[CH2:10][CH2:9]2)[CH2:4][CH2:3]1>O1CCCC1.[OH-].[Pd+2].[OH-].[C]>[NH2:30][C:27]1[CH:26]=[CH:25][C:24]([O:23][C:21]2[CH:20]=[CH:19][N:18]=[C:17]([NH:16][C:14]([N:11]3[CH2:10][CH2:9][CH:8]([N:5]4[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]4)[CH2:13][CH2:12]3)=[O:15])[CH:22]=2)=[CH:29][CH:28]=1

Participants

4

Reactant 1

HCID 231531552-{[4-(1-Methylpiperazin-4-yl)piperidin-1-yl]carbonylamino}-4-(4-nitrophenoxy)pyridine

Product 1

HCID 231533634-(4-Aminophenoxy)-2-{[4-(1-methylpiperazin-4-yl)piperidin-1-yl]carbonylamino}pyridineYield 98.1%

Reagents, catalysts & solvents 2

HCID 178502593HCID 178502593, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2-{[4-(1-Methylpiperazin-4-yl)piperidin-1-yl]carbonylamino}-4-(4-nitrophenoxy)pyridine (163 mg) was dissolved in tetrahydrofuran (20 ml). After adding 20% palladium hydroxide-carbon (104 mg), the mixture was stirred overnight under a hydrogen atmosphere. The catalyst was filtered and washed with tetrahydrofuran. The filtrate and the washings were combined and concentrated under reduced pressure, and the resultant residue was dried under reduced pressure to provide the title compound (149 mg, 98%) as pale yellow powder.

Workup

  1. filtrationThe catalyst was filtered
  2. washwashed with tetrahydrofuran
  3. concentrationconcentrated under reduced pressure
  4. dry with materialthe resultant residue was dried under reduced pressure

Sources & evidence

ORD record
ord-a7cae0d2447544969bf7806c78576e15
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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