1-((4-Methoxyphenyl)sulfonyl)piperazine → 2-{1-[4-(4-Methoxy-benzenesulfonyl)-piperazin-1-yl]-ethyl}-3H-quinazolin-4-one

HRID 238223Notes

Reaction equation

HRID 238223 reaction equation
Br[CH:2]([C:4]1[NH:13][C:12](=[O:14])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1)[CH3:3].[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([S:23]([N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)(=[O:25])=[O:24])=[CH:19][CH:18]=1>C(#N)C>[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([S:23]([N:26]2[CH2:31][CH2:30][N:29]([CH:2]([C:4]3[NH:13][C:12](=[O:14])[C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[N:5]=3)[CH3:3])[CH2:28][CH2:27]2)(=[O:25])=[O:24])=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 7975601-((4-Methoxyphenyl)sulfonyl)piperazineHCID 1355033222-(1-bromoethyl)-4(3H)-quinazolinone

Product 1

HCID 1358460552-{1-[4-(4-Methoxy-benzenesulfonyl)-piperazin-1-yl]-ethyl}-3H-quinazolin-4-oneYield 449.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a flask containing of 2-(1-bromo-ethyl)-3H-quinazolin-4-one (500.0 mg, 0.20 mmol) in acetonitrile (20 ml) was added KI (496.0 mg, 0.30 mmol), and 1-(4-methoxy-benzenesulfonyl)-piperazine (509.6 mg, 0.20 mmol). The reaction was heated for 18 hours. The solution was concentrated under reduced pressure. The residue was partitioned between water (20 ml) and dichloromethane (20 ml). The organic layer was dried over magnesium sulfate, filtered and concentrated under reduced pressure. The solvent was removed under vacuum. The resulting residue was purified by silica gel chromatography with 50% dichloromethane in hexane. The product was collected and dried under reduced pressure to give 2-{1-[4-(4-Methoxy-benzenesulfonyl)-piperazin-1-yl]-ethyl}-3H-quinazolin-4-one (Yield 385.0 mg, 45.18%). 1H NMR (400 MHz, DMSO-6): δ 1.25 (d, 3H, J=6.82 Hz), 2.67-2.56 (m, 4H), 2.88 (s, br, 4H), 3.85 (s, 3H), 3.53 (q, 1H, J=13.89, 6.82 Hz), 7.15 (d, 2H, J=8.84), 7.34 (t, 1H, J=7.33 Hz), 7.51 (d, 1H, J=8.34 Hz), 7.68-7.61 (m, 3H), 8.00 (d, 1H, J=7.83 Hz). MS m/z calc. 428.15, found (ESI); 429.4 (M+1)+. Retention time 2.68 minutes.

Workup

  1. temperatureThe reaction was heated for 18 hours
  2. concentrationThe solution was concentrated under reduced pressure
  3. customThe residue was partitioned between water (20 ml) and dichloromethane (20 ml)
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe solvent was removed under vacuum
  8. customThe resulting residue was purified by silica gel chromatography with 50% dichloromethane in hexane
  9. customThe product was collected
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-cc3300525ae34a2993980ba8f6fb22f6
Source dataset
uspto-grants-2014_02
Patent number
US08642609B2

Reaction notes

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