Ethylamine → HCID 15227516, compound

HRID 1742208Notes

Reaction equation

HRID 1742208 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH:7]=O)=[CH:3][CH:2]=1.[CH2:9]([NH2:11])[CH3:10].[BH4-].[Na+].[C:14](OC(=O)C)(=[O:16])[CH3:15].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.C1CCCCC1.O>[CH2:9]([N:11]([CH2:7][C:4]1[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=1)[C:14](=[O:16])[CH3:15])[CH3:10]

Participants

9

Reactant 5

HCID 6341EthylamineHCID 7918Acetic AnhydrideHCID 10340Sodium CarbonateHCID 133894-PyridinecarboxaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 15227516HCID 15227516, compoundYield 82%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8078CyclohexaneSolvent

Procedure

A mixture of pyridine-4-carboxaldehyde (XI; 10.71 g, 0.1 mole) and ethyl amine (12.88 g of a 70% water solution, 0.2 mole) were stirred for 20 min. Cyclohexane (75 ml) was added and the mixture was refluxed for 16 hrs under a Dean-Stark trap. The mixture was then concentrated in vacuo. Ethanol (100 ml) and sodium borohydride (five 0.4 g tablets, 50 mmole) were then added to the residue and mixture was stirred for 3 hrs in an ice bath. The mixture was concentrated in vacuo and the residue was dissolved in acetonitrile (100 ml) and filtered. Acetic anhydride (10.38 ml, 0.11 mole) was added and the reaction was stirred for 2 days. Sodium carbonate (15.9 g, 0.15 mole) was added and the solution was refluxed for 20 min. The mixture was cooled and filtered. The filtrate was concentrated in vacuo and the residue was chromatographed on silica gel using 5% methanol/ethyl acetate as the eluent to give the product (14.57 g, 82%).

Workup

  1. temperaturethe mixture was refluxed for 16 hrs under a Dean-Stark trap
  2. concentrationThe mixture was then concentrated in vacuo
  3. stirringwas stirred for 3 hrs in an ice bath
  4. concentrationThe mixture was concentrated in vacuo
  5. dissolutionthe residue was dissolved in acetonitrile (100 ml)
  6. filtrationfiltered
  7. stirringthe reaction was stirred for 2 days
  8. temperaturethe solution was refluxed for 20 min
  9. temperatureThe mixture was cooled
  10. filtrationfiltered
  11. concentrationThe filtrate was concentrated in vacuo
  12. customthe residue was chromatographed on silica gel using 5% methanol/ethyl acetate as the eluent

Sources & evidence

ORD record
ord-2e9cf0a971cf4c5597acf95377e1bfb4
Source dataset
uspto-grants-1994_08
Patent number
US05338738

Reaction notes

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