HCID 22380652, compound → HCID 22380762, compound

HRID 895635Notes

Reaction equation

HRID 895635 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][CH:9]([NH:12][C:13]2[C:18]([N+:19]([O-])=O)=[CH:17][CH:16]=[CH:15][C:14]=2[CH3:22])[CH2:8][CH2:7]1)=[O:5])[CH3:2]>O1CCCC1.[Ni].C(O)C>[NH2:19][C:18]1[CH:17]=[CH:16][CH:15]=[C:14]([CH3:22])[C:13]=1[NH:12][CH:9]1[CH2:8][CH2:7][N:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:11][CH2:10]1

Participants

5

Reactant 1

HCID 22380652HCID 22380652, compound

Product 1

HCID 22380762HCID 22380762, compoundYield 83.4%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

1-Ethoxycarbonyl-4-[(2-methyl-6-nitrophenyl)amino]piperidine (38 mg) was dissolved in tetrahydrofuran (0.4 ml), added with a suspension of Raney nickel in ethanol (0.2 ml) and stirred at 40° C. for 2 hours under hydrogen gas atmosphere. After insoluble matters were removed, the solvent was evaporated under reduced pressure. The residue was purified by preparative thin layer silica gel column chromatography (developing solvent: hexane:ethyl acetate=2:1) to obtain (28.6 mg) of the title compound. Yield: 83%.

Workup

  1. customAfter insoluble matters were removed
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was purified by preparative thin layer silica gel column chromatography (developing solvent: hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-372bc8f1766e4eddbd2d0a6be9934428
Source dataset
uspto-grants-2005_07
Patent number
US06916822B2

Reaction notes

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