1-Methylpiperazine → 4-Methyl-7-(4-methyl-1-piperazinyl)-1,2-dihydrobenzo[c]pyrrolo[1,2,3-ef][1,5]benzodiazepine

HRID 4072ノート

反応式

HRID 4072 の反応式
[CH3:1][C:2]1[CH:3]=[C:4]2[NH:10][C:9](=O)[C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[N:6]3[CH2:16][CH2:17][C:18]([CH:19]=1)=[C:5]23.[CH3:20][N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1>[Ti](Cl)(Cl)(Cl)Cl.C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:3]=[C:4]2[N:10]=[C:9]([N:24]3[CH2:25][CH2:26][N:21]([CH3:20])[CH2:22][CH2:23]3)[C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[N:6]3[CH2:16][CH2:17][C:18]([CH:19]=1)=[C:5]23

参加物

5

反応物 2

HCID 531671-MethylpiperazineHCID 138232804-Methyl-1,2-dihydrobenzo[c]pyrrolo[1,2,3-ef][1,5]benzodiazepin-7-one

生成物 1

HCID 138232734-Methyl-7-(4-methyl-1-piperazinyl)-1,2-dihydrobenzo[c]pyrrolo[1,2,3-ef][1,5]benzodiazepine

試薬・触媒・溶媒 2

HCID 24193Titanium Tetrachloride触媒HCID 1140Toluene溶媒2 回

実験手順

A solution of 4-methyl-1,2-dihydrobenzo[c]pyrrolo[1,2,3-ef][1,5]benzodiazepin-7-one (3.6 g, 14.3 mmoles), N-methylpiperazine (16 ml) and toluene (350 ml) was heated to 110° C. Titanium tetrachloride (4.3 ml) was added in three portions in two minute intervals. The mixture was heated under reflux for two hours and cooled to room temperature. Toluene (500 ml) and ice-water (500 m) were added. The mixture was stirred for 30 minutes and the insoluble material was removed by filtration. The organic phase was separated. The aqueous phase was extracted with toluene (200 ml). The combined toluene solutions were washed with water (300 ml), brine (2 times, 300 ml) and dried over anhydrous sodium sulfate. The solvent was evaporated. The residue was triturated with ethanol:hexane to a solid. Recrystallization of the solid from chloroform:hexane yielded 2.4 g of product. The mother liquor was concentrated and the residue was purified on a silica gel column (60 g, 230-400 mesh) to give a second crop of 1.3 g of product (77% overall yield). Recrystallization from 2-propanol gave the analytical sample, mp 173°-174° C.

後処理

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for two hours
  3. customthe insoluble material was removed by filtration
  4. customThe organic phase was separated
  5. extractionThe aqueous phase was extracted with toluene (200 ml)
  6. washThe combined toluene solutions were washed with water (300 ml), brine (2 times, 300 ml)
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was evaporated
  9. customThe residue was triturated with ethanol
  10. customRecrystallization of the solid from chloroform

出典と根拠

ORDレコード
ord-436f9d4d56d4444ca9533632a7256525
出典データセット
uspto-grants-1988_02
特許番号
US04723003

反応ノート

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