1-Phenylpiperazine → 1,3-Dimethyl-7-[4-(4-phenylpiperazinylmethylbenzoyl)benzyl]xanthine

HRID 1291420Notes

Reaction equation

HRID 1291420 reaction equation
BrCC1C=C[C:6]([C:7]([C:9]2[CH:28]=[CH:27][C:12]([CH2:13][N:14]3[C:22]4[C:21](=[O:23])[N:20]([CH3:24])[C:19](=[O:25])[N:18]([CH3:26])[C:17]=4[N:16]=[CH:15]3)=[CH:11][CH:10]=2)=[O:8])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[C:37]1([N:43]2[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]2)[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>CN(C=O)C.O>[CH3:24][N:20]1[C:21](=[O:23])[C:22]2[N:14]([CH2:13][C:12]3[CH:27]=[CH:28][C:9]([C:7](=[O:8])[C:6]4[CH:5]=[CH:4][C:40]([C:39]5[CH:38]=[CH:7][CH:6]=[CH:5][CH:4]=5)=[CH:41][C:42]=4[CH2:37][N:43]4[CH2:44][CH2:45][NH:46][CH2:47][CH2:48]4)=[CH:10][CH:11]=3)[CH:15]=[N:16][C:17]=2[N:18]([CH3:26])[C:19]1=[O:25]

Participants

6

Reactant 3

HCID 70961-PhenylpiperazineHCID 11430Potassium CarbonateHCID 189188217-[4-(4-Bromomethylbenzoyl)benzyl]-1,3-dimethylxanthine

Product 1

HCID 699611381,3-Dimethyl-7-[4-(4-phenylpiperazinylmethylbenzoyl)benzyl]xanthineYield 14.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 7-[4-(4-bromomethylbenzoyl)benzyl]-1,3-dimethylxanthine (232 mg), potassium carbonate (109 mg) and 1-phenylpiperazine (92 mg) in DMF (10 ml) was stirred at 60° C. for 5 hours. This reaction mixture was poured in water and extracted with ethyl acetate. The extract was washed with water, dried, and concentrated. The residue was purified by silica gel column chromatography (ethyl acetate: hexane: triethylamine =3:1:0.1) and recrystallized from chloroform-isopropyl ether to provide the title compound as colorless solid (20 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate: hexane: triethylamine =3:1:0.1)
  6. customrecrystallized from chloroform-isopropyl ether

Sources & evidence

ORD record
ord-a5f9c9ab868846a293e2d88141f08a90
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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