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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 61870
Notes
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Reaction equation

HRID 61870 reaction equation
[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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 7967CyclohexanoneHCID 82115Trimethylsilyl cyanideHCID 66834254HCID 66834254, compound

Product 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-carbonitrileYield 30%

Reagents, catalysts & solvents 3

HCID 9883512
zinc(II)iodide
Catalyst
HCID 6212ChloroformSolvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

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%).

Workup

  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))

Sources & evidence

ORD record
ord-f2f7d8e5a65e478fb48d3610106645e5
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09440922B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes