Water → N~1~-[2-(3,5-Dimethoxyphenyl)ethyl]-N~1~-methylbutane-1,4-diamine

HRID 373933Notes

Reaction equation

HRID 373933 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][C:5]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[C:7]([O:13][CH3:14])[CH:6]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:22][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:6]=[C:7]([O:13][CH3:14])[CH:8]=[C:9]([O:11][CH3:12])[CH:10]=1)[CH2:22][CH2:23][CH2:24][CH2:25][NH2:26]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 214124-BromobutyronitrileHCID 12866444HCID 12866444, compound

Product 1

HCID 15282282N~1~-[2-(3,5-Dimethoxyphenyl)ethyl]-N~1~-methylbutane-1,4-diamineYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

10.0 g of N-methyl-(2-(3,5-dimethoxyphenyl)ethyl)amine was dissolved in 130 ml of N,N-dimethylformamide, followed by the addition of 10.63 g of anhydrous potassium carbonate and 6.12 ml of 4-bromobutyronitrile. The reaction was carried out at a room temperature for 12 hours. Water was added to the reaction mixture. The obtained mixture was extracted with ethyl acetate. The ethyl acetate phase was washed with water and a saturated aqueous solution of common salt successively, dried over anhydrous potassium carbonate and distilled to remove the solvent. 150 ml of ethanol, 11 ml of concentrated hydrochloric acid and 1 g of platinum- oxide were added to the obtained residue to carry out hydrogenation at a room temperature under 3 kg/cm2 for 12 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. After the solvent had been distilled off, the residue was distilled under a reduced pressure to obtain 10.85 g of the title compound as a colorless oil (yield: 80%).

Workup

  1. extractionThe obtained mixture was extracted with ethyl acetate
  2. washThe ethyl acetate phase was washed with water
  3. dry with materiala saturated aqueous solution of common salt successively, dried over anhydrous potassium carbonate
  4. distillationdistilled
  5. customto remove the solvent
  6. addition150 ml of ethanol, 11 ml of concentrated hydrochloric acid and 1 g of platinum- oxide were added to the obtained residue
  7. customat a room temperature
  8. customfor 12 hours
  9. filtrationThe catalyst was filtered out
  10. concentrationthe filtrate was concentrated under a reduced pressure
  11. additionfollowed by the addition of concentrated aqueous ammonia
  12. extractionThe obtained mixture was extracted with chloroform
  13. dry with materialThe chloroform phase was dried over anhydrous potassium carbonate
  14. distillationAfter the solvent had been distilled off
  15. distillationthe residue was distilled under a reduced pressure

Sources & evidence

ORD record
ord-24b1ca4c25c540b49ffa9bbd371ffb89
Source dataset
uspto-grants-1992_11
Patent number
US05166188

Reaction notes

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