HCID 22353182, compound → HCID 22353175, compound

HRID 271105Notes

Reaction equation

HRID 271105 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:16][CH2:17][CH2:18][CH2:19][N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:9]=1)([O-])=O>C(O)C.[Pd]>[N:20]1([CH2:19][CH2:18][CH2:17][O:16][C:7]2[C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=2)[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1

Participants

4

Reactant 1

HCID 22353182HCID 22353182, compound

Product 1

HCID 22353175HCID 22353175, compoundYield 46.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4-[3-(5-Nitro-biphenyl-2-yloxy)-propyl]-morpholine (u, 400 mg, 1.1 mmol) was dissolved in 10 mL ethanol and hydrogenated at 1 atm. using 10% Pd—C as a catalyst. After the reaction was allowed to stir overnight, the reaction mixture was filtered and the solvent was evaporated. The residue was purified by silica gel chromatography (eluent: 5% methanol/DCM) to afford 160 mg 6-(3-morpholin-4-yl-propoxy)-biphenyl-3-ylamine (v): m/e: 312.18, MS (ES+): 313.2.

Workup

  1. filtrationthe reaction mixture was filtered
  2. customthe solvent was evaporated
  3. customThe residue was purified by silica gel chromatography (eluent: 5% methanol/DCM)

Sources & evidence

ORD record
ord-9437295001ad4400b927e47f0bd3bfa8
Source dataset
uspto-grants-2008_11
Patent number
US07452873B2

Reaction notes

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