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Tetrafluoro-m-phenylenediamine dihydrochloride → Tetrafluoro-m-phenylenediamine dihydrochloride

HRID 1472494
Notes
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Reaction equation

HRID 1472494 reaction equation
[C:1]1([NH2:12])[C:6]([F:7])=[C:5]([F:8])[C:4]([F:9])=[C:3]([NH2:10])[C:2]=1[F:11].[ClH:13].Cl.[F:15][C:16]1[CH:17]=[C:18]([N:28]2[CH2:32][CH:31]([CH2:33][NH:34]C(C3C=CC=CC=3)C)[O:30][C:29]2=[O:43])[CH:19]=[CH:20][C:21]=1[N:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1>[OH-].[OH-].[Pd+2].CO>[C:1]1([NH2:12])[C:6]([F:7])=[C:5]([F:8])[C:4]([F:9])=[C:3]([NH2:10])[C:2]=1[F:11].[ClH:13].[ClH:13].[F:15][C:16]1[CH:17]=[C:18]([N:28]2[CH2:32][CH:31]([CH2:33][NH2:34])[O:30][C:29]2=[O:43])[CH:19]=[CH:20][C:21]=1[N:22]1[CH2:23][CH2:24][O:25][CH2:26][CH2:27]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 902170523-(3-Fluoro-4-morpholinylphenyl)-5-[(1-phenylethyl)aminomethyl]-1,3-oxazolidin-2-one

Product 2

HCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 227145793-Fluoro-4-morpholinylphenyl-5-aminomethyl-1,3-oxazolidin-2-one

Reagents, catalysts & solvents 2

HCID 9942167
Palladium hydroxide
Catalyst
HCID 887MethanolSolvent

Procedure

To a reaction flask were added 3.0 g of dihydrochloride of 3-(3-fluoro-4-morpholinylphenyl)-5-[(1-phenylethyl)aminomethyl]-1,3-oxazolidin-2-one (4a), 100 ml of methanol and 1.0 g of 10% Pd(OH)2/C. Gas inside the reaction flask was evacuated and argon was then introduced to the reaction flask. The reaction mixture was allowed to react for 48 hours at room temperature with stirring. After the reaction was completed, the reaction mixture was filtered, and subsequently put under reduced pressure for solvent removal to give a dihydrochloride of 3-(3-fluoro-4-morpholinylphenyl-5-aminomethyl-1,3-oxazolidin-2-one (5a) as a white solid and at a yield of 95%.

Workup

  1. customGas inside the reaction flask was evacuated
  2. additionargon was then introduced to the reaction flask
  3. customto react for 48 hours at room temperature
  4. filtrationthe reaction mixture was filtered
  5. customsubsequently put under reduced pressure for solvent removal

Sources & evidence

ORD record
ord-09781232b5914341b4f1c078021fd588
Source dataset
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09012631B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes