4-[3-(Dimethylamino)azetidin-1-yl]piperidine-1-carboxylic acid [4-(4-nitrophenoxy)pyridin-2-yl]amide → 4-(3-Dimethylaminoazetidin-1-yl)piperidine-1-carboxylic acid [4-(4-aminophenoxy)pyridin-2-yl]amide

HRID 492900Notes

Reaction equation

HRID 492900 reaction equation
[N+:1]([C:4]1[CH:32]=[CH:31][C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]([N:18]3[CH2:23][CH2:22][CH:21]([N:24]4[CH2:27][CH:26]([N:28]([CH3:30])[CH3:29])[CH2:25]4)[CH2:20][CH2:19]3)=[O:17])[CH:10]=2)=[CH:6][CH:5]=1)([O-])=O>O1CCCC1.[OH-].[Pd+2].[OH-].[C]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]([N:18]3[CH2:19][CH2:20][CH:21]([N:24]4[CH2:25][CH:26]([N:28]([CH3:30])[CH3:29])[CH2:27]4)[CH2:22][CH2:23]3)=[O:17])[CH:10]=2)=[CH:31][CH:32]=1

Participants

4

Reactant 1

HCID 576773934-[3-(Dimethylamino)azetidin-1-yl]piperidine-1-carboxylic acid [4-(4-nitrophenoxy)pyridin-2-yl]amide

Product 1

HCID 576773374-(3-Dimethylaminoazetidin-1-yl)piperidine-1-carboxylic acid [4-(4-aminophenoxy)pyridin-2-yl]amideYield 87.8%

Reagents, catalysts & solvents 2

HCID 178502593HCID 178502593, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

After adding 20% palladium hydroxide-carbon (50 mg) to a solution of 4-[3-(dimethylamino)azetidin-1-yl]piperidine-1-carboxylic acid [4-(4-nitrophenoxy)pyridin-2-yl]amide (112 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 (91.5 mg, 87.8%) as a pale yellow oil.

Workup

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

Sources & evidence

ORD record
ord-8eedb725b8fa4487a5508bb90035f8f8
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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