1-Phenylpiperazine → 3,5-Dimethyl-2-[4-[4-(4-phenylpiperazinylmethyl)benzoyl]benzylthio]-4-(3H)-quinazolinone

HRID 1291338Notes

Reaction equation

HRID 1291338 reaction equation
[CH3:1][N:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[CH3:13])[N:4]=[C:3]1[SH:14].Br[CH2:16][C:17]1[CH:32]=[CH:31][C:20]([C:21]([C:23]2[CH:28]=[CH:27][C:26]([CH2:29]Br)=[CH:25][CH:24]=2)=[O:22])=[CH:19][CH:18]=1.[CH:33]1[CH:34]=[CH:35][C:36]([N:39]2[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]2)=[CH:37][CH:38]=1.[OH-].[Na+].O>CN(C=O)C>[CH3:1][N:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[CH3:13])[N:4]=[C:3]1[S:14][CH2:16][C:17]1[CH:32]=[CH:31][C:20]([C:21](=[O:22])[C:23]2[CH:28]=[CH:27][C:26]([CH2:29][N:42]3[CH2:43][CH2:44][N:39]([C:36]4[CH:37]=[CH:38][CH:33]=[CH:34][CH:35]=4)[CH2:40][CH2:41]3)=[CH:25][CH:24]=2)=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 70961-PhenylpiperazineHCID 23039244,4'-Bis(bromomethyl)benzophenoneHCID 23719242Sodium hydroxide--water (1/1/1)HCID 178424003HCID 178424003, compound

Product 1

HCID 189193243,5-Dimethyl-2-[4-[4-(4-phenylpiperazinylmethyl)benzoyl]benzylthio]-4-(3H)-quinazolinoneYield 13.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3,5-dimethyl-2-mercapto-4(3H)quinazolinone (1.03 g), 4,4'-bis (bromomethyl)benzophenone (1.75 g), phenylpiperazine (810 mg), and 1N-sodium hydroxide/water (5.5 ml) in DMF (35 ml) was stirred at 60° C. for 1 hour. This reaction mixture was concentrated and the residue was dissolved in ethyl acetate, washed with water, dried, and concentrated. The residue was purified by silica gel column chromatography (hexane: ethyl acetate: chloroform=4:1:1) and crystallized from isopropyl ether to provide the title compound as colorless solid (372 mg).

Workup

  1. concentrationThis reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (hexane: ethyl acetate: chloroform=4:1:1)
  7. customcrystallized from isopropyl ether

Sources & evidence

ORD record
ord-dcf868e8660447f697a6bd0b1b68183c
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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