Stannous chloride dihydrate → HCID 69145023, compound

HRID 444967Notes

Reaction equation

HRID 444967 reaction equation
[CH2:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:11]=[N:12][C:13]([N+:16]([O-])=O)=[CH:14][CH:15]=2)[CH2:6][CH2:5]1)[CH:2]=[CH2:3].O.O.[Sn](Cl)Cl>CO>[CH2:1]([N:4]1[CH2:5][CH2:6][N:7]([C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[N:12][CH:11]=2)[CH2:8][CH2:9]1)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 69146057HCID 69146057, compound

Product 1

HCID 69145023HCID 69145023, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

300 mg (1.21 mmol) of 1-allyl-4-(6-nitropyridin-3-yl)piperazine from Example 15.1 were dissolved in 20 ml of methanol, after which 2.18 g (9.67 mmol) of tin(II) chloride dihydrate were added and the mixture was stirred at 70° C. for 2 hours. After the solvent had been evaporated down to dryness, the resulting residue was treated with water and this mixture was made alkaline using a dilute aqueous solution of sodium hydroxide and extracted with ethyl acetate. The solid which had precipitated out was filtered off with suction. The phases were then separated and the aqueous phase was extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and evaporated down to dryness, with 183 mg (69% of theory) of the title compound being obtained.

Workup

  1. customAfter the solvent had been evaporated down to dryness
  2. additionthe resulting residue was treated with water
  3. extractionextracted with ethyl acetate
  4. customThe solid which had precipitated out
  5. filtrationwas filtered off with suction
  6. customThe phases were then separated
  7. extractionthe aqueous phase was extracted three times with ethyl acetate
  8. dry with materialThe combined organic phases were dried over sodium sulfate
  9. filtrationfiltered
  10. customevaporated down to dryness, with 183 mg (69% of theory) of the title compound
  11. custombeing obtained

Sources & evidence

ORD record
ord-9601ae5c7bdf4b6eaafd72f2e3eba580
Source dataset
uspto-grants-2013_07
Patent number
US08476275B2

Reaction notes

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