Triethylamine → 2-(Methoxycarbonyl)-5-nitrophenyl 4-methylpiperazine-1-carboxylate

HRID 230066노트

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HRID 230066 반응식
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:5]=1[OH:13].ClC(Cl)(O[C:19](=[O:25])OC(Cl)(Cl)Cl)Cl.C(N(C(C)C)CC)(C)C.CCN(CC)CC.[CH3:43][N:44]1[CH2:49][CH2:48][NH:47][CH2:46][CH2:45]1>C1COCC1.C(Cl)Cl>[CH3:43][N:44]1[CH2:49][CH2:48][N:47]([C:19]([O:13][C:5]2[CH:6]=[C:7]([N+:10]([O-:12])=[O:11])[CH:8]=[CH:9][C:4]=2[C:3]([O:2][CH3:1])=[O:14])=[O:25])[CH2:46][CH2:45]1

참가 물질

8

반응물 5

HCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 139539Salicylic acid, 4-nitro-, methyl ester

생성물 1

HCID 576329252-(Methoxycarbonyl)-5-nitrophenyl 4-methylpiperazine-1-carboxylate

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

To a dry flask are added 2-hydroxy-4-nitro-benzoic acid methyl ester (40 mmol) (from Example 1h) and triphosgene (26.6 mmol) and DCM (100 mL). The reaction mixture is cooled to 0° C. and diisopropylethylamine (40 mmol) is added slowly. After addition the mixture is warmed to rt. After 1 h at this temperature it is refluxed for 1 h. The mixture is cooled down and the solvents are removed. THF (100 mL), Et3N (80 mmol), and N-methyl piperazine (80 mmol) are added and the mixture is stirred at rt overnight. The solvent is removed and the residue dissolved in EtOAc. Phases are separated upon addition of a 10% solution of NaHCO3. The organic phase is washed with brine, dried on Na2SO4 and evaporated. The crude is used in the following reaction.

후처리

  1. additionAfter addition the mixture
  2. temperatureis warmed to rt
  3. temperatureAfter 1 h at this temperature it is refluxed for 1 h
  4. temperatureThe mixture is cooled down
  5. customthe solvents are removed
  6. customThe solvent is removed
  7. dissolutionthe residue dissolved in EtOAc
  8. customPhases are separated upon addition of a 10% solution of NaHCO3
  9. washThe organic phase is washed with brine
  10. customdried on Na2SO4
  11. customevaporated
  12. customThe crude is used in the following reaction

출처 및 근거

ORD 기록
ord-ff89afc63ad34974acc5de0ac8fb91c3
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07563894B2

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