Water → HCID 9993837, compound

HRID 1647241Notes

Reaction equation

HRID 1647241 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([O:13][CH3:14])[CH:6]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH:22]([CH3:27])[CH2:23][CH2:24][C:25]#[N:26].O>CN(C)C=O>[CH3:1][N:2]([CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([O:13][CH3:14])[CH:6]=1)[CH2:27][CH2:22][CH2:23][CH2:24][CH2:25][NH2:26]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 77039N-MethylhomoveratrylamineHCID 85740Pentanenitrile, 4-bromo-

Product 1

HCID 9993837HCID 9993837, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.5 g of N-methyl-(2-(3,4-dimethoxyphenyl)ethyl)amine was dissolved in 25 ml of N,N-dimethylformamide, followed by the addition of 1.95 g of anhydrous potassium carbonate and 1.65 ml of 4-bromovaleronitrile. The obtained mixture was reacted at a room temperature for 16 hours, followed by the addition of water. The obtained mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and a saturated aqueous solution of common salt, dried over anhydrous potassium carbonate and distilled to remove the solvent. 40 ml of ethanol, 3.2 ml of concentrated hydrochloric acid and 0.3 g of platinum oxide were added to the obtained residue to carry out hydrogenation at a room temperature under 3 kg/cm2 for 6 hours. The catalyst was filtered out and the filtrate was concentrated under a reduced pressure, followed by the addition of concentrated aqueous ammonia. The obtained mixture was extracted with chloroform. The chloroform phase was dried over anhydrous potassium carbonate and distilled to remove the solvent. The residue was purified by silica gel column chromatography [solvent: dichloromethane/methanol/concentrated aqueous ammonia (100:10:1)] to obtain 1.95 g of the title compound as a yellow oil (yield: 55%).

Workup

  1. customThe obtained mixture was reacted at a room temperature for 16 hours
  2. extractionThe obtained mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materiala saturated aqueous solution of common salt, dried over anhydrous potassium carbonate
  5. distillationdistilled
  6. customto remove the solvent
  7. addition40 ml of ethanol, 3.2 ml of concentrated hydrochloric acid and 0.3 g of platinum oxide were added to the obtained residue
  8. customat a room temperature
  9. customfor 6 hours
  10. filtrationThe catalyst was filtered out
  11. concentrationthe filtrate was concentrated under a reduced pressure
  12. additionfollowed by the addition of concentrated aqueous ammonia
  13. extractionThe obtained mixture was extracted with chloroform
  14. dry with materialThe chloroform phase was dried over anhydrous potassium carbonate
  15. distillationdistilled
  16. customto remove the solvent
  17. customThe residue was purified by silica gel column chromatography [solvent: dichloromethane/methanol/concentrated aqueous ammonia (100:10:1)]

Sources & evidence

ORD record
ord-534af3fc44dd4bfaa1fa5423abeae26b
Source dataset
uspto-grants-1995_07
Patent number
US05430059

Reaction notes

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