Methanol → 3-Fluoro-4-morpholinoaniline

HRID 2207058Notes

Reaction equation

HRID 2207058 reaction equation
CO.[F:3][C:4]1[CH:5]=[C:6]([N+:16]([O-])=O)[CH:7]=[CH:8][C:9]=1[N:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1>[Ni].O>[F:3][C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][C:9]=1[N:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1)[NH2:16]

Participants

5

Reactant 2

HCID 887MethanolHCID 29054894-(2-Fluoro-4-nitrophenyl)morpholine

Product 1

HCID 14853303-Fluoro-4-morpholinoanilineYield 90.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 962WaterSolvent

Conditions

Temperature
47.5 °C

Procedure

Methanol (1.35 Lt) and 3-fluoro-4-morpholinyl nitrobenzene (134 gr) are added into autoclave and followed by Raney Nickel (20.5 gr). The system was flushed with nitrogen and hydrogen gas. The pressure of hydrogen was set to 4.0 kg/cm−2. The reaction mixture was stirred at 45-50° C. under H2 pressure for 8 hrs & the reaction followed by TLC until completion. The reaction mixture was filtered through celite and the filtrate is distilled off evaporate solvent completely U/vacuum at <50° C. temperature. Reaction mass is cooled to 25-30° C. To this DM water (400 ml) is added, Stirred for 1 hr at 25-30° C. The solid is filtered to give 105 gr of 3-fluoro-4-morpholinyl aniline.

Workup

  1. customThe system was flushed with nitrogen and hydrogen gas
  2. filtrationThe reaction mixture was filtered through celite
  3. distillationthe filtrate is distilled off
  4. customevaporate solvent completely U/vacuum at <50° C. temperature
  5. customReaction mass
  6. temperatureis cooled to 25-30° C
  7. stirringStirred for 1 hr at 25-30° C
  8. filtrationThe solid is filtered

Sources & evidence

ORD record
ord-ff9dae2ca9094a92886fcc29803708bb
Source dataset
uspto-grants-2016_06
Patent number
US09376407B2

Reaction notes

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