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

HRID 4032Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 4032
[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

Komponenten

5

Edukt 3

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

Produkt 1

HCID 1382331610-Bromo-9-methyl-6-(4-methyl-1-piperazinyl)-1,2-dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepineAusbeute 11,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-c6cdf19ab61f40fc890ba6f32e88d976
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04723007

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