Stannous Chloride → 4-(1-Benzyl-pyrrolidin-3-yl)-2-fluoro-phenylamine

HRID 1260259Notes

Reaction equation

HRID 1260259 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[C:15]([F:22])[CH:14]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Sn](Cl)Cl>CO>[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([C:13]2[CH:18]=[CH:17][C:16]([NH2:19])=[C:15]([F:22])[CH:14]=2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 57470088HCID 57470088, compound

Product 1

HCID 574944484-(1-Benzyl-pyrrolidin-3-yl)-2-fluoro-phenylamineYield 80.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-Benzyl-3-(3-fluoro-4-nitro-phenyl)-pyrrolidine (550 mg, 1.83 mmol) was dissolved in methanol (30 ml), tin dichloride (3.125 g, 16.48 mmol) was added, and the reaction mixture stirred at reflux for 2 h. The methanol was evaporated, 1 N sodium hydroxide (60 ml) and ethyl acetate were added and stirring continued. The tin salts were filtered off, the organic phase was separated, dried over magnesium sulfate, filtered, and the solvent evaporated under reduced pressure to yield an oil (400 mg).

Workup

  1. temperatureat reflux for 2 h
  2. customThe methanol was evaporated
  3. addition1 N sodium hydroxide (60 ml) and ethyl acetate were added
  4. stirringstirring
  5. filtrationThe tin salts were filtered off
  6. customthe organic phase was separated
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-3e5fe9b1d3dc48ee9da10f1a24316082
Source dataset
uspto-grants-2013_06
Patent number
US08470810B2

Reaction notes

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