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Cyclohexanone → 8-[4-(1-Cyano-cyclohexyl)-piperazin-1-yl]-9-ethyl-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

HRID 2275246
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HRID 2275246 반응식
[CH2:1]([C:3]1[C:24]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[CH:23][C:6]2[C:7]([CH3:22])([CH3:21])[C:8]3[NH:9][C:10]4[C:15]([C:16]=3[C:17](=[O:18])[C:5]=2[CH:4]=1)=[CH:14][CH:13]=[C:12]([C:19]#[N:20])[CH:11]=4)[CH3:2].[C:31]1(=O)[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1.C[Si]([C:42]#[N:43])(C)C>C(Cl)(Cl)Cl.C(OCC)(=O)C.[I-].[Zn+2].[I-]>[C:42]([C:31]1([N:28]2[CH2:29][CH2:30][N:25]([C:24]3[C:3]([CH2:1][CH3:2])=[CH:4][C:5]4[C:17](=[O:18])[C:16]5[C:15]6[C:10](=[CH:11][C:12]([C:19]#[N:20])=[CH:13][CH:14]=6)[NH:9][C:8]=5[C:7]([CH3:22])([CH3:21])[C:6]=4[CH:23]=3)[CH2:26][CH2:27]2)[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1)#[N:43]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 7967CyclohexanoneHCID 82115Trimethylsilyl cyanideHCID 66834254HCID 66834254, 화합물

생성물 1

HCID 668349718-[4-(1-Cyano-cyclohexyl)-piperazin-1-yl]-9-ethyl-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile수율 30%

시약·촉매·용매 3

HCID 9883512zinc(II)iodide촉매
HCID 6212
Chloroform
용매
HCID 8857Ethyl Acetate용매

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온도
60 °C

실험 절차

9-Ethyl-6,6-dimethyl-11-oxo-8-piperazin-1-yl-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile (45 mg) and cyclohexanone (25 mg) were suspended in chloroform (2 ml), added with trimethylsilyl cyanide (30 mg) and zinc iodide (5 mg), and the mixture was stirred at 60° C. for 17 hrs. The reaction mixture was diluted with ethyl acetate (20 ml) and the organic layer was washed with 10% brine solution and concentrated under reduced pressure. The resulting residues were purified by silica gel column (dichloromethane/methanol (=99/1)) to obtain the title compound (12 mg, yield 30%).

후처리

  1. washthe organic layer was washed with 10% brine solution
  2. concentrationconcentrated under reduced pressure
  3. customThe resulting residues were purified by silica gel column (dichloromethane/methanol (=99/1))

출처 및 근거

ORD 기록
ord-c14ed9213fd14209abc26bc49f833c96
출처 데이터셋
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09126931B2

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