HCID 53698819, compound → HCID 19038223, compound

HRID 263466Notes

Reaction equation

HRID 263466 reaction equation
C([O:8][C:9]1[CH:24]=[CH:23][C:12]([CH:13]=[CH:14][C:15]([N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[O:16])=[CH:11][C:10]=1[N+:25]([O-])=O)C1C=CC=CC=1>CO.[Pd]>[OH:8][C:9]1[CH:24]=[CH:23][C:12]([CH2:13][CH2:14][C:15]([N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[O:16])=[CH:11][C:10]=1[NH2:25]

Participants

4

Reactant 1

HCID 53698819HCID 53698819, compound

Product 1

HCID 19038223HCID 19038223, compoundYield 103.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

0.5 g of N-(4-benzyloxy-3-nitrocinnamoyl)piperidine (prepared as described in Example 12) was dissolved in 30 ml of methanol. 300 mg of 10% palladium-on-carbon were added to the solution, which was then catalytically reduced whilst bubbling hydrogen through it, under atmospheric pressure for 60 minutes. The catalyst was then removed by filtration, and the methanol was removed by distillation under reduced pressure. The resulting residue was purified by silica gel column chromatography, using ethyl acetate as the eluent, to afford 0.35 g of the title compound as crystals, melting at 149°-150° C.

Workup

  1. customwhilst bubbling hydrogen through it
  2. customThe catalyst was then removed by filtration
  3. customthe methanol was removed by distillation under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e89d5d123d6040a188945d5a5addb958
Source dataset
uspto-grants-1997_07
Patent number
US05643925

Reaction notes

Loading…