1-Benzylpiperazine → HCID 19911547, compound

HRID 1708917Notes

Reaction equation

HRID 1708917 reaction equation
[C:1]1([CH2:7][N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[CH2:15][C:16]1[N:17]([CH2:25][CH2:26][O:27][CH2:28][CH3:29])[C:18]2[C:23]([N:24]=1)=[CH:22][N:21]=[CH:20][N:19]=2.C(=O)([O-])O.[Na+]>C(O)C>[CH2:28]([O:27][CH2:26][CH2:25][N:17]1[C:16]([CH2:15][N:11]2[CH2:10][CH2:9][N:8]([CH2:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:13][CH2:12]2)=[N:24][C:23]2[C:18]1=[N:19][CH:20]=[N:21][CH:22]=2)[CH3:29]

Participants

5

Reactant 3

HCID 759941-BenzylpiperazineHCID 516892Sodium BicarbonateHCID 19911498HCID 19911498, compound

Product 1

HCID 19911547HCID 19911547, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4.4 parts of 1-(phenylmethyl)piperazine, 4.7 parts of 8-(chloromethyl)-9-(2-ethoxyethyl)-9H-purine, 2.1 parts of sodium hydrogen carbonate and 40 parts of ethanol was stirred and refluxed for 5 hours. The reaction mixture was evaporated and the residue was taken up in water. The product was extracted with trichloromethane. The extract was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (97:3 by volume) as eluent. The pure fractions were collected and the eluent was evaporated, yielding 4.6 parts (62.0%) of 9-(2-ethoxyethyl)-8-[[4-(phenylmethyl)-1-piperazinyl]methyl]-9H-purine as a residue (compound 23).

Workup

  1. temperaturerefluxed for 5 hours
  2. customThe reaction mixture was evaporated
  3. extractionThe product was extracted with trichloromethane
  4. customThe extract was dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography over silica gel using
  8. additiona mixture of trichloromethane and methanol (97:3 by volume) as eluent
  9. customThe pure fractions were collected
  10. customthe eluent was evaporated

Sources & evidence

ORD record
ord-0ed11eca8d3b479381d3694dbe4371d0
Source dataset
uspto-grants-1990_08
Patent number
US04946843

Reaction notes

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