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Potassium Carbonate → 2-fluoro-N-(3-morpholinopropyl)-4-nitroaniline

HRID 56164
Notes
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Reaction equation

HRID 56164 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1.C([O-])([O-])=O.[K+].[K+].[F:17][C:18]1[CH:24]=[C:23]([N+:25]([O-:27])=[O:26])[CH:22]=[CH:21][C:19]=1[NH2:20]>C(#N)C>[F:17][C:18]1[CH:24]=[C:23]([N+:25]([O-:27])=[O:26])[CH:22]=[CH:21][C:19]=1[NH:20][CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 958344-(3-Chloropropyl)morpholineHCID 1012542-Fluoro-4-nitroaniline

Product 1

HCID 29277432-fluoro-N-(3-morpholinopropyl)-4-nitroanilineYield 63%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 4-(3-chloropropyl)morpholine (1.64 g, 10 mmol) and K2CO3 (4.14 g, 30 mmol) in acetonitrile (20 mL) was added 2-fluoro-4-nitroaniline (1.56 g, 10 mmol) dropwise. The mixture was stirred at rt for 24 h, then filtered and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1) to give the title compound as yellow oil (1.78 g, 63%).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1)

Sources & evidence

ORD record
ord-55cd3e8f63cc46f28c0689e6fb518f7f
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09434695B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes