Potassium Carbonate → N-[2-(3,4-Dimethoxyphenyl)ethyl]homopiperazine

HRID 974994

Reaction equation

HRID 974994 reaction equation
[NH:1]1[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH3:8][O:9][C:10]1[CH:11]=[C:12]([CH2:18][CH2:19]Cl)[CH:13]=[CH:14][C:15]=1[O:16][CH3:17].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:8][O:9][C:10]1[CH:11]=[C:12]([CH2:18][CH2:19][N:1]2[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]2)[CH:13]=[CH:14][C:15]=1[O:16][CH3:17]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 68163Hexahydro-1,4-diazepineHCID 30153594-(2-Chloroethyl)-1,2-dimethoxybenzene

Product 1

HCID 15023608N-[2-(3,4-Dimethoxyphenyl)ethyl]homopiperazineYield 77.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

32.27 g of homopiperazine, 13.2 g of 2-(3,4-dimethoxyphenyl)ethyl chloride and 71.3 g of potassium carbonate were added to 500 ml of acetonitrile. The obtained mixture was heated under reflux for 20 hours, cooled and filtered. The filtrate was concentrated under a reduced pressure to obtain a residue. This residue was extracted with ether thrice. The extracts were combined, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under a reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent: chloroform/methanol/isopropylamine (100:10:1)) to obtain 13.40 g of the title compound as a yellow oil (yield: 77%).

Workup

  1. temperatureThe obtained mixture was heated
  2. temperatureunder reflux for 20 hours
  3. temperaturecooled
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under a reduced pressure
  6. customto obtain a residue
  7. extractionThis residue was extracted with ether thrice
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated under a reduced pressure
  11. customThe obtained residue was purified by silica gel column chromatography (solvent: chloroform/methanol/isopropylamine (100:10:1))

Sources & evidence

ORD record
ord-14df1013ddaf490bb330846c98e166b5
Source dataset
uspto-grants-1997_03
Patent number
US05607953

Linked notes

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