Hydrochloric Acid → 1-[3-{4-(diphenylmethyl)piperazin-1-yl}propyl]-3-methyl-2,4(1H,3H)quinazolinedione

HRID 365103Notes

Reaction equation

HRID 365103 reaction equation
Br[CH2:2][CH2:3][CH2:4][N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8](=[O:15])[N:7]([CH3:16])[C:6]1=[O:17].[C:18]1([CH:24]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CO.O.CN(C)C=O>[C:31]1([CH:24]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:25]2[CH2:26][CH2:27][N:28]([CH2:2][CH2:3][CH2:4][N:5]3[C:14]4[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=4)[C:8](=[O:15])[N:7]([CH3:16])[C:6]3=[O:17])[CH2:29][CH2:30]2)[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 70048BenzhydrylpiperazineHCID 136872081-(3-bromopropyl)-3-methyl-2,4(1H)-quinazolinedione

Product 1

HCID 134883851-[3-{4-(diphenylmethyl)piperazin-1-yl}propyl]-3-methyl-2,4(1H,3H)quinazolinedione

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1-(3-bromopropyl)-3-methyl-2,4(1H,3H)-quinazolinedione (1.68 g), 1-diphenylmethylpiperazine (1.56 g), anhydrous potassium carbonate (2.33 g) and N,N-dimethylformamide (8 ml) was stirred for 3 hours at 60° C. After cooling, water was added to the reaction mixture and then the mixture was extracted twice with chloroform. The chloroform layer was washed with water and with saturated sodium chloride aqueous solution respectively, dried over anhydrous magnesium sulfate and evaporated in vacuo to give an oily residue. This oily residue was dissolved in methanol and then conc.hydrochloric acid solution was dropwise added to the solution to give a crystal, which was collected by filtration, washed with water and dried. This crude crystal was recrystallized from a mixture of methanol and water, to give 1-[3-{4-(diphenylmethyl)piperazin-1-yl}propyl]-3-methyl-2,4(1H,3H)quinazolinedione.2HCl.0.5H2O (2.4 g).

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted twice with chloroform
  3. washThe chloroform layer was washed with water and with saturated sodium chloride aqueous solution respectively
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated in vacuo
  6. customto give an oily residue
  7. customto give a crystal, which
  8. filtrationwas collected by filtration
  9. washwashed with water
  10. customdried
  11. customThis crude crystal was recrystallized from a mixture of methanol and water

Sources & evidence

ORD record
ord-4df21c82b8664ed6b898e16aec93f1d1
Source dataset
uspto-grants-1986_08
Patent number
US04608375

Reaction notes

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