Diphenyl Ether → HCID 178516358, compound

HRID 964994Notes

Reaction equation

HRID 964994 reaction equation
COC(N1[CH2:10][CH2:9][N:8]([C:11]2[CH:12]=[C:13]([CH:15]=[CH:16][CH:17]=2)[NH2:14])CC1)=O.[CH:18]([O-])([O-])OCC.CC1(C)O[C:30](=O)[CH2:29][C:27](=O)[O:26]1.C1(OC2C=CC=CC=2)C=CC=CC=1>CCCCCC>[OH:26][C:27]1[C:15]2[C:13](=[C:12]3[C:11](=[CH:17][CH:16]=2)[N:8]=[CH:9][CH:10]=[CH:18]3)[N:14]=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 7583Diphenyl EtherHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 19075045HCID 19075045, compoundHCID 53630039Ethylorthoformate

Product 1

HCID 178516358HCID 178516358, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 3-(4-methoxycarbonyl-1-piperazinyl)aniline (0.75 g, 3.2 mmol), ethyl orthoformate (0.50 g, 3.4 mmol), Meldrum's acid (0.48 g, 3.4 mmol) was stirred at 110° C. for 1.5 hours. The reaction mixture was added with diphenyl ether (10 ml) and stirred at 240° C. for 1.5 hours. After allowing to cool, n-hexane was added to the mixture. The resulting precipitates were collected by filtration and purified by column chromatography (Wako Gel™ C-200, methylene chloride methanol=10 : 1) to obtain the titled compound (320 mg, 35%).

Workup

  1. stirringstirred at 240° C. for 1.5 hours
  2. temperatureto cool
  3. customThe resulting precipitates
  4. filtrationwere collected by filtration
  5. custompurified by column chromatography (Wako Gel™ C-200, methylene chloride methanol=10 : 1)

Sources & evidence

ORD record
ord-517bbb2f9ed549249894f628b7e15985
Source dataset
uspto-grants-1998_06
Patent number
US05773449

Reaction notes

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