HCID 7062386, compound → HCID 6930630, compound

HRID 1713807Notes

Reaction equation

HRID 1713807 reaction equation
[CH3:1][C@H:2]1[O:7][C@@H:6]([CH3:8])[CH2:5][N:4]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=2)[CH2:3]1>[Pd].C(O)C>[CH3:8][C@H:6]1[O:7][C@@H:2]([CH3:1])[CH2:3][N:4]([C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)[CH2:5]1

Participants

4

Reactant 1

HCID 7062386HCID 7062386, compound2×

Product 1

HCID 6930630HCID 6930630, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of cis-2,6-dimethyl-4-(4-nitrophenyl)morpholine (Intermediate 68, 8.0 g) and 10% palladium on carbon (800 mg) in ethanol (100 mL) was stirred under an atmosphere of hydrogen at 50° C. for 6 h. The mixture was filtered and the filtrate was concentrated by evaporation to give the title compound (4.3 g, 100%) as an oil which subsequently solidified; 1H NMR δ (CDCl3): 6.79 (2H, d), 6.65 (2H, d), 3.81 (2H, m), 3.25 (2H, d), 2.33, (2H, t), 1.23 (6H, d); MS m/e MH+: 207.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated by evaporation

Sources & evidence

ORD record
ord-7a19876f3bec496f9f0047c810dc5e80
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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