Allylamine → HCID 19600254, compound

HRID 611056Notes

Reaction equation

HRID 611056 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([CH:6]=O)=[CH:2]1.[CH2:8]([NH2:11])[CH:9]=[CH2:10].[BH4-].[Na+].[OH-].[Na+]>CO>[CH2:8]([NH:11][CH2:6][C:3]1[CH:4]=[CH:5][O:1][CH:2]=1)[CH:9]=[CH2:10]

Participants

6

Reactant 4

HCID 7853AllylamineHCID 103513-FuraldehydeHCID 14798Sodium HydroxideHCID 4311764Sodium borohydride

Product 1

HCID 19600254HCID 19600254, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 6.019 g (62.64 mmol) of 3-furaldehyde and 5.37 g (94.0 mmol) of allylamine in 100 ml of methanol was stirred at room temperature for 0.5 hours. To this reaction mixture, 4.74 g (125 mmol) of sodium borohydride was added portionwise under ice-cooling, followed by stirring at room temperature for 1 hour. The reaction mixture was poured into an aqueous sodium hydroxide and extracted with dichloromethane 3 times. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=1/1 to ethyl acetate) to yield N-allyl-3-furylmethylamine.

Workup

  1. temperaturecooling
  2. extractionextracted with dichloromethane 3 times
  3. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=1/1 to ethyl acetate)

Sources & evidence

ORD record
ord-dc4653fe8ad24505ba8b22f1fac78414
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

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