Hydrochloric Acid → 2,3a,10-trimethyl-6-phenyl-2,3,3a,4-tetrahydro-1H-indolo[3,2,1-ij][1,6]naphthyridine

HRID 576534Notes

Reaction equation

HRID 576534 reaction equation
[C:1]1([CH3:9])[CH:6]=[CH:5][C:4]([NH:7]N)=[CH:3][CH:2]=1.Cl.[CH3:11][N:12]1[CH2:17][CH2:16][C:15](=O)[C:14]([CH3:29])([CH2:19][CH2:20][C:21](=O)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:13]1>>[CH3:11][N:12]1[CH2:17][C:16]2[C:3]3[CH:2]=[C:1]([CH3:9])[CH:6]=[CH:5][C:4]=3[N:7]3[C:15]=2[C:14]([CH3:29])([CH2:19][CH:20]=[C:21]3[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:13]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 10875(4-Methylphenyl)hydrazineHCID 673571101,3-Dimethyl-3-(3-oxo-3-phenyl-propyl)-piperidin-4-one

Product 1

HCID 533781662,3a,10-trimethyl-6-phenyl-2,3,3a,4-tetrahydro-1H-indolo[3,2,1-ij][1,6]naphthyridine

Procedure

A solution of p-tolylhydrazine.HCl (13 mg, 0.084 mmol) and 1,3-dimethyl-3-(3-oxo-3-phenyl-propyl)-piperidin-4-one (22 mg, 0.084 mmol) in ethanolic-HCl (5 mL) was stirred at 84° C. for 12 h. The reaction mixture was concentrated under reduced pressure and the residue was basified with saturated aqueous NaHCO3 solution. The product was extracted with EtOAc (3×15 mL), organic layer dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by reverse phase HPLC to obtain 2,3a,10-trimethyl-6-phenyl-2,3,3a,4-tetrahydro-1H-indolo[3,2,1-ij][1,6]naphthyridine.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionThe product was extracted with EtOAc (3×15 mL), organic layer
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-8fe7ea6532d94ad481d030282755d2ab
Source dataset
uspto-grants-2015_05
Patent number
US09040519B2

Reaction notes

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