HCID 86612986, compound → HCID 67106814, compound

HRID 1012115Notes

Reaction equation

HRID 1012115 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[C:19]([N+:26]([O-])=O)[CH:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CN(C=O)C.CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]([NH2:23])=[C:19]([NH2:26])[CH:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 1

HCID 86612986HCID 86612986, compound

Product 1

HCID 67106814HCID 67106814, compoundYield 100.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

4-[2-(3,4-Dinitro-phenoxy)-ethyl]-piperidine-1-carboxylic acid tert-butyl ester (0.12 g, 0.3 mmol) was dissolved in DMF (3 ml) under an atmosphere of nitrogen. Pd/C (10%, 0.012 g) was added and the reaction mixture was shaken under a hydrogen atmosphere for 24 h. The reaction mixture was diluted with methanol (20 ml) and insoluble material was removed by filtration. The filtrate was reduced in vacuo to give 4-[2-(3,4-diamino-phenoxy)-ethyl]-piperidine-1-carboxylic acid tert-butyl ester as a brown oil (0.101 g, 100%). (LC/MS: Rt 2.21, [M+H]+ 336.16).

Workup

  1. customwas removed by filtration

Sources & evidence

ORD record
ord-7af0412b74f143afa7705692a94f5e41
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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