4-(3-Nitro-5-trifluoromethyl-benzoyl)-morpholine → Morpholine, 4-[3-amino-5-(trifluoromethyl)benzoyl]-

HRID 871499Notes

Reaction equation

HRID 871499 reaction equation
[N:1]1([C:7]([C:9]2[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[C:11]([N+:19]([O-])=O)[CH:10]=2)=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1>C(OCC)(=O)C.[Pd]>[N:1]1([C:7]([C:9]2[CH:10]=[C:11]([NH2:19])[CH:12]=[C:13]([C:15]([F:16])([F:18])[F:17])[CH:14]=2)=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 219549894-(3-Nitro-5-trifluoromethyl-benzoyl)-morpholine

Product 1

HCID 66876746Morpholine, 4-[3-amino-5-(trifluoromethyl)benzoyl]-Yield 96.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Morpholin-4-yl-(3-nitro-5-trifluoromethyl-phenyl)-methanone (800 mg, 2.6 mmoles) from the previous step was dissolved in 40 mL of ethyl acetate. To this solution was added 10% palladium on carbon, the reaction was stirred under hydrogen at room temperature overnight. The solution filtered through celite and concentrated to give 3-(morpholine-4-carbonyl)-5-(trifluoromethyl)phenylamine (688 mg). 1H NMR (300 MHz, DMSO-d6) δ 6.90 (s, 1H), 6.75 (d, 2H), 5.6 (b, 6H).

Workup

  1. filtrationThe solution filtered through celite and
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-78e89cff155d469baf7857ba30cce78b
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

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