Cyclohexene → HCID 15380624, compound

HRID 1275547Notes

Reaction equation

HRID 1275547 reaction equation
[CH3:1][N:2]([CH3:46])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[C:24]2[C:12](=[C:13]([CH3:45])[C:14]3[N:15]([CH3:44])[C:16]4[CH:17]=[CH:18][C:19]([O:25][C:26]([N:28]5[CH2:33][CH2:32][N:31](C(OCC6C=CC=CC=6)=O)[CH2:30][CH2:29]5)=[O:27])=[CH:20][C:21]=4[C:22]=3[CH:23]=2)[CH:11]=[CH:10][N:9]=1)=[O:7].C1CCCCC=1>CO.[Pd]>[CH3:1][N:2]([CH3:46])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[C:24]2[C:12](=[C:13]([CH3:45])[C:14]3[N:15]([CH3:44])[C:16]4[CH:17]=[CH:18][C:19]([O:25][C:26]([N:28]5[CH2:29][CH2:30][NH:31][CH2:32][CH2:33]5)=[O:27])=[CH:20][C:21]=4[C:22]=3[CH:23]=2)[CH:11]=[CH:10][N:9]=1)=[O:7]

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 15380625HCID 15380625, compound

Product 1

HCID 15380624HCID 15380624, compoundYield 78.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2.6 g of 1-[(2-dimethylaminoethyl)aminocarbonyl]-5,6-dimethyl-9-[(4-benzyloxycarbonyl-piperazino)carbonyloxy]-6H-pyrido[4,3-b]carbazole, 5 ml of cyclohexene and 1 g of 10% palladium-on-carbon in 260 ml of methanol are refluxed for 45 minutes. The catalyst is removed by filtration and the filtrate is concentrated to dryness. The residue is chromatographed on silica using a mixture of dichloromethane, methanol and ammonia (85:15:1) as eluant. The product obtained is washed with diethyl ether and ethanol to yield 1.6 g of the desired product, m.p.(cap): 230-234° C.

Workup

  1. customThe catalyst is removed by filtration
  2. concentrationthe filtrate is concentrated to dryness
  3. customThe residue is chromatographed on silica using
  4. additiona mixture of dichloromethane, methanol and ammonia (85:15:1) as eluant
  5. customThe product obtained
  6. washis washed with diethyl ether and ethanol

Sources & evidence

ORD record
ord-92735c537997436f876a9b6ccd0f6c12
Source dataset
uspto-grants-2000_12
Patent number
US06162811

Reaction notes

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