Ethyl Acetate → 2-fluoro-N1-(4-morpholinobutyl)benzene-1,4-diamine

HRID 56170Notes

Reaction equation

HRID 56170 reaction equation
[F:1][C:2]1[CH:18]=[C:17]([N+:19]([O-])=O)[CH:16]=[CH:15][C:3]=1[NH:4][CH2:5][CH2:6][CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1.CCOC(C)=O>[Pd].CO>[F:1][C:2]1[CH:18]=[C:17]([NH2:19])[CH:16]=[CH:15][C:3]=1[NH:4][CH2:5][CH2:6][CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 1179660642-fluoro-N-(4-morpholinobutyl)-4-nitroaniline

Product 1

HCID 900228942-fluoro-N1-(4-morpholinobutyl)benzene-1,4-diamineYield 100.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-fluoro-N-(4-morpholinobutyl)-4-nitroaniline (1.19 g, 4.00 mmol) in mixed solvents of EtOAc (20 mL) and MeOH (20 mL) was added catalyst Pd/C (0.30 g). The reaction was stirred at rt under H2 for 2 h, then filtered. The filtrate was concentrated in vacuo. The residue was purified by a silica gel column chromatography (EtOAc/MeOH (V/V)=10:1) to give the title compound as a white solid (1.07 g, 100%).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo
  3. customThe residue was purified by a silica gel column chromatography (EtOAc/MeOH (V/V)=10:1)

Sources & evidence

ORD record
ord-87e1bf0e606140608f23961aa60a268a
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

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