1,4-Dioxane → HCID 19087650, compound

HRID 1464289Notes

Reaction equation

HRID 1464289 reaction equation
[C:1]1([C:7]2[CH2:8][CH2:9][N:10]([CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]3[CH:26]=[CH:25][CH:24]=[C:23]([N+:27]([O-:29])=[O:28])[C:19]=3[C:20]([NH2:22])=[O:21])[CH2:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:30]1CCOC[CH2:31]1>>[C:1]1([C:7]2[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][CH2:15][CH2:16][N:17]3[C:18]4[C:19](=[C:23]([N+:27]([O-:29])=[O:28])[CH:24]=[CH:25][CH:26]=4)[C:20](=[O:21])[NH:22][C:31]3=[O:30])[CH2:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 312751,4-DioxaneHCID 19087676HCID 19087676, compound

Product 1

HCID 19087650HCID 19087650, compound

Conditions

Temperature
150 °C

Procedure

A mixture of 2-[4-(4-phenyl-1,2,3,6-tetrahydropyridin-1-yl)butylamino]-6-nitrobenzamide (300 mg) and N,N'-carbonyldiimidazole (554 mg) in dioxane (3 ml) was stirred for 2 hours at 150° C. The solvent was removed during the reaction. The residue was crystallized from a mixture of ethanol and ether. The crude crystalline materials were collected, washed with methylene chloride, and recrystallized from ethanol to afford 1-[4-(4-phenyl-1,2,3,6-tetrahydropyridin-1-yl)butyl]-5-nitro-2,4(1H,3H)-quinazolinedione (265 mg).

Workup

  1. customThe solvent was removed during the reaction
  2. customThe residue was crystallized from a mixture of ethanol and ether
  3. customThe crude crystalline materials were collected
  4. washwashed with methylene chloride
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-af334564ed734dd9b56774f7d2e3e007
Source dataset
uspto-grants-1994_04
Patent number
US05304560

Reaction notes

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