Formamide → HCID 17986924, compound

HRID 1444548Notes

Reaction equation

HRID 1444548 reaction equation
[C:1]1([C:7]2[CH:15]=[CH:14][C:10]([CH2:11][CH2:12][NH2:13])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:16](OC)=O.C(N)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1.ClCCl>[C:1]1([C:7]2[CH:8]=[CH:9][C:10]([CH2:11][CH2:12][NH:13][CH3:16])=[CH:14][CH:15]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 713FormamideHCID 7865Methyl formateHCID 282102-(4-Biphenyl)ethylamineHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 17986924HCID 17986924, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

4-Phenylphenethyl amine, 0.48 g (2.4 mmol), was added to an excess of methyl formate (5 mL) and dichloromethane (5 mL) was added to improve solubility. The heterogeneous reaction mixture was refluxed to give a solution within 20 hours. NMR analysis of a sample showed almost complete conversion to N-formyl amine. The reaction mixture was evaporated to give 0.47 g (87%). The formyl compound, 0.47 g (2.09 mmol), was dissolved in THF and 2.1 mL of 1.0 M lithium aluminium hydride (2.1 mmol) in THF was added. TLC analysis after 20 hours showed only starting material and 2 mL (2 mmol) of lithium aluminium hydride solution was added. Analysis after 1 hour showed starting material and the mixture was heated to reflux. After 1.5 hours a precipitate was formed, the starting material consumed and tetrahydrofuran (15 ml) was added. The mixture was quenched by successive addition of water (0.15 g), 15% aqueous sodium hydroxide (0.15 g) and water (0.45 g). The mixture was filtered and evaporated to give 0.33 g crude product. The crude product was purified by silica gel chromatography (100 mL) using dichloromethane/methanol/concentrated ammonia (90+10+1) as eluant. Evaporation of pure fractions gave 78 mg (18%) of the sub-titled compound.

Workup

  1. additionwas added
  2. temperatureThe heterogeneous reaction mixture was refluxed
  3. customto give a solution within 20 hours
  4. customThe reaction mixture was evaporated
  5. customto give 0.47 g (87%)
  6. waitAnalysis after 1 hour showed starting
  7. temperaturematerial and the mixture was heated to reflux
  8. customAfter 1.5 hours a precipitate was formed
  9. customthe starting material consumed
  10. additiontetrahydrofuran (15 ml) was added
  11. customThe mixture was quenched by successive addition of water (0.15 g), 15% aqueous sodium hydroxide (0.15 g) and water (0.45 g)
  12. filtrationThe mixture was filtered
  13. customevaporated
  14. customto give 0.33 g crude product
  15. customThe crude product was purified by silica gel chromatography (100 mL)
  16. customEvaporation of pure fractions

Sources & evidence

ORD record
ord-2b59ccab3d0e42ccaef2e287a58e1472
Source dataset
uspto-grants-2010_02
Patent number
US07662845B2

Reaction notes

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