3-Furaldehyde → N-(3-furylmethyl)-6-phenylhexylamine

HRID 611076Notes

Reaction equation

HRID 611076 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]2[C:17](=[O:18])[C:16]3=CC=C[CH:22]=[C:15]3[C:14]2=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.NN.[OH-].[Na+].O1C=CC(C=O)=C1.[BH4-].[Na+]>C(O)C>[O:18]1[CH:17]=[CH:16][C:15]([CH2:14][NH:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:22]1

Participants

7

Reactant 5

HCID 103513-FuraldehydeHCID 14798Sodium Hydroxide2×HCID 24654Hydrazine hydrate (1:1)HCID 4311764Sodium borohydrideHCID 19599919N-(6-phenylhexyl)phthalimide

Product 1

HCID 19599977N-(3-furylmethyl)-6-phenylhexylamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 9.138 g (29.73 mmol) of N-(6-phenylhexyl)phthalimide and 2.16 ml (44.6 mmol) of hydrazine monohydrate in 100 ml of ethanol was refluxed for 1 hour. After cooling to room temperature, the reaction mixture was poured into 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 6-phenylhexylamine was dissolved in 100 ml of methanol; 2.86 g (29.7 mmol) of 3-furaldehyde was added, followed by stirring at room temperature for 0.5 hours, after which 2.25 g (59.5 mmol) of sodium borohydride was added under ice-cooling, followed by stirring at room temperature for 1 hour. The reaction mixture was poured into 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 crude product was purified by silica gel column chromatography (hexane/ethyl acetate=1/1 to ethyl acetate) to yield the desired product.

Workup

  1. extractionextracted with dichloromethane 3 times
  2. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. dissolutionThe resulting crude 6-phenylhexylamine was dissolved in 100 ml of methanol
  5. temperaturecooling
  6. stirringby stirring at room temperature for 1 hour
  7. extractionextracted with dichloromethane 3 times
  8. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  9. distillationthe solvent was distilled off under reduced pressure
  10. customThe crude product was purified by silica gel column chromatography (hexane/ethyl acetate=1/1 to ethyl acetate)

Sources & evidence

ORD record
ord-11a258bb3331449ea2e9e9bfa4933804
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

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