Dichloromethane → 10-Bromo-9-methyl-6-(4-methyl-1-piperazinyl)-1,2-dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepine

HRID 978287ノート

反応式

HRID 978287 の反応式
[Br:1]N1C(=O)CCC1=O.[CH3:9][N:10]1[CH2:15][CH2:14][N:13]([C:16]2[C:22]3[CH:23]=[CH:24][CH:25]=[C:26]4[CH2:27][CH2:28][N:20]([C:21]=34)[C:19]3[CH:29]=[CH:30][C:31]([CH3:33])=[CH:32][C:18]=3[N:17]=2)[CH2:12][CH2:11]1.ClCCl>CN(C)C=O>[Br:1][C:30]1[C:31]([CH3:33])=[CH:32][C:18]2[N:17]=[C:16]([N:13]3[CH2:12][CH2:11][N:10]([CH3:9])[CH2:15][CH2:14]3)[C:22]3[CH:23]=[CH:24][CH:25]=[C:26]4[CH2:27][CH2:28][N:20]([C:21]=34)[C:19]=2[CH:29]=1

参加物

5

反応物 3

HCID 6344DichloromethaneHCID 67184N-bromobutanimideHCID 138232916-(4-Methyl-1-piperazinyl)-9-methyl-1,2-dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepine

生成物 1

HCID 1382331610-Bromo-9-methyl-6-(4-methyl-1-piperazinyl)-1,2-dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepine収率 11.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

A solution of N-bromosuccinimide (0.91 g, 5.1 mmoles) in dimethylformamide (3 ml) was added dropwise to a solution of 6-(4-methyl-1-piperazinyl)-9-methyl-1,2-dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepine (1.6 g, 4.8 mmoles) in dimethylformamide (30 ml) at 0°-3° C. The reaction mixture was stirred for 30 minutes. The solution was poured into dichloromethane (250 ml), and was washed with brine (4 times, 150 ml), and dried over anhydrous magnesium sulfate. The solvent was removed at reduced pressure and the residue was dried. Purification was accomplished by flash chromatography on an aluminium oxide column (grade III, 60 g), eluted with dichloromethane (500 ml) and 2% methanol in dichloromethane (250 ml). The fractions containing the product were pooled and concentrated. Recrystallization from 2-propanol:water (1:1, 20 ml) yielded 230 mg (11.6%) of product, mp 177°-177° C.

後処理

  1. washwas washed with brine (4 times, 150 ml)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was removed at reduced pressure
  4. customthe residue was dried
  5. customPurification
  6. washeluted with dichloromethane (500 ml) and 2% methanol in dichloromethane (250 ml)
  7. additionThe fractions containing the product
  8. concentrationconcentrated
  9. customRecrystallization from 2-propanol:water (1:1, 20 ml)

出典と根拠

ORDレコード
ord-5d8ebd100b3048aea08055431ddaef47
出典データセット
uspto-grants-1987_05
特許番号
US04663453

反応ノート

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