Hydrochloric Acid → 4-allyl-2,4,8-trimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

HRID 576530Notes

Reaction equation

HRID 576530 reaction equation
[C:1]1([CH3:9])[CH:6]=[CH:5][C:4]([NH:7]N)=[CH:3][CH:2]=1.Cl.[CH2:11]([C:14]1([CH3:22])[C:19](=O)[CH2:18][CH2:17][N:16]([CH3:21])[CH2:15]1)[CH:12]=[CH2:13].OS(O)(=O)=O>O1CCOCC1>[CH2:11]([C:14]1([CH3:22])[C:19]2[NH:7][C:4]3[CH:3]=[CH:2][C:1]([CH3:9])=[CH:6][C:5]=3[C:18]=2[CH2:17][N:16]([CH3:21])[CH2:15]1)[CH:12]=[CH2:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 10875(4-Methylphenyl)hydrazineHCID 137400223-Allyl-1,3-dimethyl-piperidin-4-one

Product 1

HCID 673559434-allyl-2,4,8-trimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a stirred solution of p-tolylhydrazine.HCl (1.2 g, 7.56 mmol) and 3-allyl-1,3-dimethyl-piperidin-4-one (1.5 g, 9.077 mmol) in 1,4-dioxane (12 mL) at 25° C. was added conc. H2SO4 (1 mL). The reaction mixture was heated at 100° C. for 30 min after which the dioxane layer was decanted and residue was basified with saturated aqueous NaHCO3 solution. The product was extracted with EtOAc (3×50 mL), organic layer dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain 1.7 g of 4-allyl-2,4,8-trimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole as a solid.

Workup

  1. customwas decanted
  2. extractionThe product was extracted with EtOAc (3×50 mL), organic layer
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5e46251a688347c5a6e48453857e8fe9
Source dataset
uspto-grants-2015_05
Patent number
US09040519B2

Reaction notes

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