Trifluoroacetic acid → HCID 67355974, compound

HRID 576511Notes

Reaction equation

HRID 576511 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5](=O)[C:4]([CH3:18])([CH2:9][C:10]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)=[CH2:11])[CH2:3]1.F[C:20](F)(F)[C:21](O)=O.O1[CH2:31][CH2:30]OCC1>>[CH3:1][N:2]1[CH2:3][C:4]([CH3:18])([CH2:9][C:10]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)=[CH2:11])[C:5]2[NH:2][C:3]3[CH:4]=[CH:5][C:21]([CH3:20])=[CH:30][C:31]=3[C:6]=2[CH2:7]1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 312751,4-DioxaneHCID 67328948HCID 67328948, compound

Product 1

HCID 67355974HCID 67355974, compound

Conditions

Temperature
100 °C

Procedure

P-Tolylhydrazinehydrochloride (150 mg, 0.94 mmol) and 1,3-dimethyl-3-(2-pyridin-4-yl-allyl)-piperidin-4-one (347 mg, 1.4 mmol) were dissolved in 1,4-dioxane (5 mL). Trifluoroacetic acid (0.3 mL) was added and the reaction mixture was heated to 100° C. for 16 h. The reaction mixture was concentrated under reduced pressure and residue was basified with saturated aqueous sodium bicarbonate. The product was extracted with EtOAc (3×30 mL), organic layer was washed with water (2×20 mL), dried over sodium sulfate and concentrated. The residue was purified by reverse phase chromatography to obtain 15 mg of 2,4,8-trimethyl-4-(2-pyridin-4-yl-allyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure and residue
  2. extractionThe product was extracted with EtOAc (3×30 mL), organic layer
  3. washwas washed with water (2×20 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by reverse phase chromatography

Sources & evidence

ORD record
ord-07189da6a60c4f99863d520e51f949db
Source dataset
uspto-grants-2015_05
Patent number
US09040519B2

Reaction notes

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