4-Methyl-3-nitroaniline → N-(4-Methyl-3-nitro-phenyl)-4-(4-methyl-piperazin-1-ylmethyl)-benzamide

HRID 273293

反応式

HRID 273293 の反応式
[CH3:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH2:12]([N:14]([CH:18]([CH3:20])C)[CH:15]([CH3:17])C)[CH3:13].Cl[CH2:22][C:23]1C=C[CH:29]=[CH:28][C:24]=1[C:25](Cl)=[O:26].[CH3:32][N:33]1CCNCC1>O1CCCC1>[CH3:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:25](=[O:26])[C:24]2[CH:28]=[CH:29][C:20]([CH2:18][N:14]3[CH2:12][CH2:13][N:33]([CH3:32])[CH2:17][CH2:15]3)=[CH:22][CH:23]=2)=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

参加物

6

反応物 4

HCID 83904-Methyl-3-nitroanilineHCID 531671-MethylpiperazineHCID 81531DiisopropylethylamineHCID 30163952-(Chloromethyl)benzoyl chloride

生成物 1

HCID 29984087N-(4-Methyl-3-nitro-phenyl)-4-(4-methyl-piperazin-1-ylmethyl)-benzamide収率 95%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
27.5 °C

実験手順

4-methyl-3-nitroaniline (30.0 g, 0.197 mol) is added to a mixture of tetrahydrofuran (120 ml) and N-ethyl-N,N-diisopropyl-amine at 23-25° C. over a period of 5 to 10 min. To this solution chloromethyl-benzoylchloride (38.4 g, 0.20 mol) dissolved in tetrahydrofuran (35 ml) is added over a period of 60-65 min maintaining a temperature of 25-30° C. The reaction mixture is stirred at this temperature for 30 min and then added to N-methylpiperazine (138.2 g, 1.38 mol) over a period of 60 to 90° C. maintaining a temperature of 25-30° C. The resulting suspension is stirred at this temperature for 60 min. Tetrahydrofurane is distilled of at 50° C. under reduced pressure. At the end of the distillation the temperature is adjusted to 45-48° C. and water (300 ml) Is added over a period of 45-60 min at this temperature. The resulting suspension is cooled to 23° C. and stirred for 60 min. The suspension is filtered, the filtercake washed with water (225 ml) and dried in vacuo to give 69.2 g of the title compound (95% of theory) as an of-white powder (99.5% area by HPLC).

後処理

  1. additionis added over a period of 60-65 min
  2. temperaturemaintaining a temperature of 25-30° C
  3. stirringThe resulting suspension is stirred at this temperature for 60 min
  4. distillationTetrahydrofurane is distilled of at 50° C. under reduced pressure
  5. distillationAt the end of the distillation the temperature
  6. customis adjusted to 45-48° C.
  7. additionwater (300 ml) Is added over a period of 45-60 min at this temperature
  8. temperatureThe resulting suspension is cooled to 23° C.
  9. stirringstirred for 60 min
  10. filtrationThe suspension is filtered
  11. washthe filtercake washed with water (225 ml)
  12. customdried in vacuo

出典と根拠

ORDレコード
ord-78ac638a4eb542d69102a19e47ccffc2
出典データセット
uspto-grants-2008_11
特許番号
US07456283B2

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