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

HRID 230066

反応式

HRID 230066 の反応式
[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

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ff89afc63ad34974acc5de0ac8fb91c3
出典データセット
uspto-grants-2009_07
特許番号
US07563894B2

関連ノート

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