Potassium Iodide → HCID 19087708, compound

HRID 1464283Notes

Reaction equation

HRID 1464283 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=[O:16])[NH:8][C:7]1=[O:17].Cl.[CH2:19]([O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)[CH2:20][CH3:21].[I-].[K+].C(=O)([O-])[O-].[Na+].[Na+]>C(C(C)=O)C(C)C>[CH2:19]([O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[N:29]1[CH2:34][CH2:33][N:32]([CH2:2][CH2:3][CH2:4][CH2:5][N:6]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9](=[O:16])[NH:8][C:7]2=[O:17])[CH2:31][CH2:30]1)[CH2:20][CH3:21]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 19087669HCID 19087669, compoundHCID 22449610HCID 22449610, compound

Product 1

HCID 19087708HCID 19087708, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 1-(4-chlorobutyl)-2,4(1H,3H)-quinazolinedione (160 mg), N-(2-propoxyphenyl)piperazine hydrochloride (178 mg), potassium iodide (105 mg), and sodium carbonate (200 mg) in methyl isobutyl ketone (15 ml) was refluxed for 5 hours. After dilution with ethyl acetate, the reaction mixture was washed in turn with water and brine, dried over magnesium sulfate, and evaporated. The residue was chromatographed on silica gel (15 g) eluting with chloroform-methanol (50:1 V/V) to give 1-[4-{4-(2-propoxyphenyl)piperazin-1-yl}butyl]-2,4(1H,3H)-quinazolinedione (266 mg).

Workup

  1. temperaturewas refluxed for 5 hours
  2. washAfter dilution with ethyl acetate, the reaction mixture was washed in turn with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue was chromatographed on silica gel (15 g)
  6. washeluting with chloroform-methanol (50:1 V/V)

Sources & evidence

ORD record
ord-eadd1c6f218e46adbbee1e1ca86e3a8d
Source dataset
uspto-grants-1994_04
Patent number
US05304560

Reaction notes

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