Hydrochloric Acid → 9-Ethyl-6,6-dimethyl-11-oxo-8-(4-oxopiperidin-1-yl)-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

HRID 61878Notes

Reaction equation

HRID 61878 reaction equation
O1[C:5]2([CH2:10][CH2:9][N:8]([C:11]3[C:12]([CH2:33][CH3:34])=[CH:13][C:14]4[C:26](=[O:27])[C:25]5[C:24]6[C:19](=[CH:20][C:21]([C:28]#[N:29])=[CH:22][CH:23]=6)[NH:18][C:17]=5[C:16]([CH3:31])([CH3:30])[C:15]=4[CH:32]=3)[CH2:7][CH2:6]2)[O:4]CC1.Cl.[OH-].[Na+]>C1COCC1.C(OCC)(=O)C>[CH2:33]([C:12]1[C:11]([N:8]2[CH2:7][CH2:6][C:5](=[O:4])[CH2:10][CH2:9]2)=[CH:32][C:15]2[C:16]([CH3:31])([CH3:30])[C:17]3[NH:18][C:19]4[C:24]([C:25]=3[C:26](=[O:27])[C:14]=2[CH:13]=1)=[CH:23][CH:22]=[C:21]([C:28]#[N:29])[CH:20]=4)[CH3:34]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 668346798-(1,4-Dioxa-8-aza-spiro[4.5]dec-8-yl)-9-ethyl-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

Product 1

HCID 668350689-Ethyl-6,6-dimethyl-11-oxo-8-(4-oxopiperidin-1-yl)-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrileYield 64%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

8-(1,4-Dioxa-8-aza-spiro[4.5]dec-8-yl)-9-ethyl-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile, which had been prepared in Example 809, was dissolved in THF (10 ml), added with 5 N hydrochloric acid (50 ml), and the mixture was stirred for 17 hrs. The reaction mixture was neutralized with 5 N aqueous solution of sodium hydroxide and diluted with ethyl acetate (200 ml). The organic layer was washed with 10% brine, and then concentrated under reduced pressure. The resulting residues were purified by silica gel column (dichloromethane/methanol=99/1 to 90/10) to obtain the title compound (2.9 g, two step yield 64%).

Workup

  1. washThe organic layer was washed with 10% brine
  2. concentrationconcentrated under reduced pressure
  3. customThe resulting residues were purified by silica gel column (dichloromethane/methanol=99/1 to 90/10)

Sources & evidence

ORD record
ord-8606ccbc8cb34a6eac99f312a5237b9a
Source dataset
uspto-grants-2016_09
Patent number
US09440922B2

Reaction notes

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