Ammonia → HCID 24852915, compound

HRID 551806Notes

Reaction equation

HRID 551806 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]2[CH2:11][CH2:10][N:9]([C:12]([N:14]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[NH:17][CH2:16][CH2:15]3)=[O:13])[CH2:8]2)[CH:2]=1.[C:24](OC(=O)C)(=[O:26])[CH3:25].N>O>[C:24]([N:17]1[C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:14]([C:12]([N:9]2[CH2:10][CH2:11][CH:7]([C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)[CH2:8]2)=[O:13])[CH2:15][CH2:16]1)(=[O:26])[CH3:25]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 7918Acetic AnhydrideHCID 67188496HCID 67188496, compound

Product 1

HCID 24852915HCID 24852915, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.25 g of 1-[(3-(pyridin-3-yl)pyrrolidin-1-yl)carbonyl]-1,2,3,4-tetrahydroquinoxaline and 1.05 ml of acetic anhydride are placed in a 10 ml round-bottomed flask. The reaction medium is brought to reflux for two hours and then a solution of ammonia in water is added at 0° C. The aqueous phase is extracted three times with ethyl acetate. The organic phases are combined and dried over sodium sulfate and the solvent is evaporated under reduced pressure. The residue is chromatographed on silica gel with a dichloromethane/methanol 95/5 mixture. 0.284 g of 1-acetyl-4-[(3-(pyridin-3-yl)pyrrolidin-1-yl)carbonyl]-1,2,3,4-tetrahydroquinoxaline is obtained.

Workup

  1. temperatureto reflux for two hours
  2. extractionThe aqueous phase is extracted three times with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. customthe solvent is evaporated under reduced pressure
  5. customThe residue is chromatographed on silica gel with a dichloromethane/methanol 95/5 mixture

Sources & evidence

ORD record
ord-016945c0d0284f72bee23f29cda7a706
Source dataset
uspto-grants-2011_05
Patent number
US07947834B2

Reaction notes

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