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Dimethyl Sulfoxide → 2,4-Bis(4-methyl-1-piperazinyl)-3H-1,5-benzodiazepine

HRID 1782395
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HRID 1782395 반응식
[N:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]([NH2:12])[CH2:3][C:2]=1[NH2:13].CS(C)=O.[CH3:18][N:19]1[CH2:24][CH2:23]N[CH2:21][CH2:20]1>C1(C)C=CC=CC=1>[CH3:18][N:19]1[CH2:24][CH2:23][N:12]([C:4]2[CH2:3][C:2]([N:13]3[CH2:21][CH2:20][N:19]([CH3:18])[CH2:24][CH2:23]3)=[N:1][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=3[N:5]=2)[CH2:21][CH2:20]1
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참가 물질

5

반응물 3

HCID 679Dimethyl SulfoxideHCID 531671-MethylpiperazineHCID 156194603H-[1,5]Benzodiazepine-2,4-diamine

생성물 1

HCID 117248372,4-Bis(4-methyl-1-piperazinyl)-3H-1,5-benzodiazepine수율 74%

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
120 °C

실험 절차

3H-[1,5]Benzodiazepine-2,4-diamine (32.50 g, 160 mmol, 86%) was added to a solution of dimethyl sulfoxide (220 ml), toluene (220 ml) and 1-methylpiperazine (165 ml). The mixture was heated for 16 h at 120° C. After cooling the product precipitated. It was filtered off and washed with isopropyl ether (80 ml) to give 40.1 g (74%) of the title compound as off-white needles. The second crop was obtained by adding isopropyl ether (410 ml) to the filtrate. The mixture was allowed to stand overnight at 4° C., the crystallised product was filtered off to give additional 4.25 g (8%) of the title compound. For analytical purposes the product was recrystallised from ethyl acetate.

후처리

  1. temperatureAfter cooling the product
  2. customprecipitated
  3. filtrationIt was filtered off
  4. washwashed with isopropyl ether (80 ml)

출처 및 근거

ORD 기록
ord-582cb0c430004610875bfb0ff5aad5c3
출처 데이터셋
uspto-grants-2009_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07498433B2

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