HCID 58072318, compound → HCID 58072523, compound

HRID 1895229Notes

Reaction equation

HRID 1895229 reaction equation
[F:1][C:2]1[C:7]([F:8])=[C:6]([N+:9]([O-])=O)[CH:5]=[CH:4][C:3]=1[N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1>CCO.[Pd]>[F:8][C:7]1[C:2]([F:1])=[C:3]([N:12]2[CH2:13][CH2:14][O:15][CH2:16][CH2:17]2)[CH:4]=[CH:5][C:6]=1[NH2:9]

Participants

4

Reactant 1

HCID 58072318HCID 58072318, compound

Product 1

HCID 58072523HCID 58072523, compoundYield 86.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4-(2,3-difluoro-4-nitrophenyl)morpholine (11.5 g, 47 mmol) and 10% Pd—C (50% wet, 1.2 g) in EtOH (150 mL) was hydrogenated for 5 h at room temperature. The reaction mixture was filtered by celite and the filtrate was concentrated under reduced pressure. The residue was recrystallized from iPr2O/AcOEt to give the title compound (8.7 g, 86% yield) as a pale red powder: 1H NMR (300 MHz, DMSO-d6): δ ppm 2.77-2.95 (4H, m), 3.60-3.79 (4H, m), 5.07 (2H, s), 6.49 (1H, td, J=9.0, 1.9 Hz), 6.62 (1H, td, J=8.9, 2.3 Hz). LC-MS (ESI) ink 215 [M+H]+.

Workup

  1. filtrationThe reaction mixture was filtered by celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was recrystallized from iPr2O/AcOEt

Sources & evidence

ORD record
ord-d97532e8dc3943e6927224537ca8a3f1
Source dataset
uspto-grants-2013_08
Patent number
US08513251B2

Reaction notes

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