HCID 10355555, compound → HCID 58980882, compound

HRID 1181346Notes

Reaction equation

HRID 1181346 reaction equation
[N+:1]([C:4]1[CH:17]=[CH:16][C:7]([O:8][CH:9]2[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]2)=[C:6]([O:18][CH3:19])[CH:5]=1)([O-])=O.[H][H]>C(O)C.[Pd]>[CH3:19][O:18][C:6]1[CH:5]=[C:4]([CH:17]=[CH:16][C:7]=1[O:8][CH:9]1[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]1)[NH2:1]

Participants

5

Reactant 2

HCID 10355555HCID 10355555, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58980882HCID 58980882, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 4-[4-nitro-2-methoxyphenoxy]-1-methylpiperidine (2.17 g, 8.15 mmol, in ethanol (150 mL) was added 10% palladium on cabon (400 mg). The mixture was subjected to 1 atm hydrogen with stirring overnight. Removal of the catalyst by filtration and evaporation of the solvent yielded the product (1.75 g, 91%). 1H NMR (CDCl3) δ 1.81-2,04 (4H, m), 2.34 (5H, m), 2.81 (2H, m), 3.56 (2H, br s), 3.80 (3H, s), 4.04 (1H, s), 6.20 (1H, dd, J=2.7 Hz, J′=8.4 Hz), 6.29 (1H,d, J=2.5 Hz), 6.77 (1 H, d, J=8.3 Hz). LCMS m/z=237 (m+H+).

Workup

  1. customRemoval of the catalyst
  2. filtrationby filtration and evaporation of the solvent

Sources & evidence

ORD record
ord-85a72e594c644952a5323180de2e13b3
Source dataset
uspto-grants-2007_10
Patent number
US07285557B2

Reaction notes

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