Stannous Chloride → HCID 57494450, compound

HRID 1260269Notes

Reaction equation

HRID 1260269 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:15][CH2:14][CH2:13][N:12]([CH2:16][CH2:17][CH3:18])[CH2:11]2)=[CH:6][CH:5]=1)([O-])=O.[Sn](Cl)Cl>CO>[CH2:16]([N:12]1[CH2:13][CH2:14][CH2:15][CH:10]([C:7]2[CH:6]=[CH:5][C:4]([NH2:1])=[CH:9][CH:8]=2)[CH2:11]1)[CH2:17][CH3:18]

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 23358037HCID 23358037, compound

Product 1

HCID 57494450HCID 57494450, compoundYield 110.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-(4-Nitro-phenyl)-1-propyl-piperidine (5.2 g, 1.86 mmol) was dissolved in methanol (35 ml), tin dichloride (3.78 g, 16.74 mmol) was added, and the reaction mixture stirred at reflux for 2 h and overnight at room temperature. The methanol was evaporated, 1 N sodium hydroxide (50 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 the crude product (450 mg, 90% purity).

Workup

  1. customThe methanol was evaporated
  2. addition1 N sodium hydroxide (50 ml) and ethyl acetate were added
  3. stirringstirring
  4. filtrationThe tin salts were filtered off
  5. customthe organic phase was separated
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-b3da4e9051e84dc5bcf77601cfc20700
Source dataset
uspto-grants-2013_06
Patent number
US08470810B2

Reaction notes

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