4-[2-(3-Methoxy-4-nitrophenoxy)ethyl]morpholine → HCID 58748494, compound

HRID 2234367Notes

Reaction equation

HRID 2234367 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][C:17]=1[N+:18]([O-])=O)[O:6][CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1>C(O)C.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:6][CH2:7][CH2:8][N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH:15]=[CH:16][C:17]=1[NH2:18]

Participants

4

Reactant 1

HCID 587483904-[2-(3-Methoxy-4-nitrophenoxy)ethyl]morpholine2×

Product 1

HCID 58748494HCID 58748494, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To 4-[2-(3-methoxy-4-nitro-phenoxy)ethyl]morpholine (Intermediate 48; 16.97 g, 60 mmol, 1 eq) in ethanol (120 mL) was added 10% palladium on charcoal (850 mg, 5% wt). The reaction was stirred at room temperature for 19 hours. After filtering off the palladium residues the solvent was evaporated under reduced pressure. The product was dissolved in ethyl acetate (100 ml) and extracted twice with 2M HCl. The aqueous layers were combined, washed with ethyl acetate then basified by the addition of 2N NaOH. The basic layer was re-acidified and captured onto mp-TsOH resin. After washing several times with methanol the product was released using 10% ammonia in methanol. After evaporation in vacuo the title compound was obtained as a dark brown oil. (14.5 g, 89%)

Workup

  1. filtrationAfter filtering off the palladium residues the solvent
  2. customwas evaporated under reduced pressure
  3. dissolutionThe product was dissolved in ethyl acetate (100 ml)
  4. extractionextracted twice with 2M HCl
  5. washwashed with ethyl acetate
  6. additionthen basified by the addition of 2N NaOH
  7. washAfter washing several times with methanol the product
  8. customAfter evaporation in vacuo the title compound
  9. customwas obtained as a dark brown oil

Sources & evidence

ORD record
ord-e8f70d57a0ff44f98145a39225bf11ea
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

Loading…