1-[1-(2-Dimethylaminoethyl)piperidin-4-yl]-1-methyl-3-[4-(4-nitrophenoxy)pyridin-2-yl]urea → 3-[4-(4-Aminophenoxy)pyridin-2-yl]-1-[1-(2-dimethylaminoethyl)piperidin-4-yl]-1-methylurea

HRID 492898Notes

Reaction equation

HRID 492898 reaction equation
[CH3:1][N:2]([CH3:32])[CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][CH:8]([N:11]([CH3:31])[C:12]([NH:14][C:15]2[CH:20]=[C:19]([O:21][C:22]3[CH:27]=[CH:26][C:25]([N+:28]([O-])=O)=[CH:24][CH:23]=3)[CH:18]=[CH:17][N:16]=2)=[O:13])[CH2:7][CH2:6]1>O1CCCC1.[OH-].[Pd+2].[OH-].[C]>[NH2:28][C:25]1[CH:24]=[CH:23][C:22]([O:21][C:19]2[CH:18]=[CH:17][N:16]=[C:15]([NH:14][C:12](=[O:13])[N:11]([CH:8]3[CH2:9][CH2:10][N:5]([CH2:4][CH2:3][N:2]([CH3:1])[CH3:32])[CH2:6][CH2:7]3)[CH3:31])[CH:20]=2)=[CH:27][CH:26]=1

Participants

4

Reactant 1

HCID 231530861-[1-(2-Dimethylaminoethyl)piperidin-4-yl]-1-methyl-3-[4-(4-nitrophenoxy)pyridin-2-yl]urea

Product 1

HCID 231531743-[4-(4-Aminophenoxy)pyridin-2-yl]-1-[1-(2-dimethylaminoethyl)piperidin-4-yl]-1-methylureaYield 69.8%

Reagents, catalysts & solvents 2

HCID 178502593HCID 178502593, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

After adding 20% palladium hydroxide-carbon (50 mg) to a solution of 1-[1-(2-dimethylaminoethyl)piperidin-4-yl]-1-methyl-3-[4-(4-nitrophenoxy)pyridin-2-yl]urea (186 mg) in tetrahydrofuran (5.0 ml), the mixture was stirred for 12 hours at room temperature under a hydrogen atmosphere. The catalyst was filtered. The filtrate was concentrated to provide the title compound (121 mg, 69.8%) as a pale yellow oil.

Workup

  1. filtrationThe catalyst was filtered
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-8dfd38c3d8414af68b401c6c0eef4e75
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

Loading…