2-Vinylpyridine → HCID 59368249, compound

HRID 1045561Notes

Reaction equation

HRID 1045561 reaction equation
[CH3:1][N:2]1[CH2:15][CH2:14][C:13]2[C:12]3[CH:11]=[C:10]([CH3:16])[CH:9]=[CH:8][C:7]=3[NH:6][C:5]=2[CH2:4][CH2:3]1.[OH-].[Na+].[CH:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1)=[CH2:20]>O>[CH3:1][N:2]1[CH2:15][CH2:14][C:13]2[C:12]3[CH:11]=[C:10]([CH3:16])[CH:9]=[CH:8][C:7]=3[N:6]([CH2:20][CH2:19][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)[C:5]=2[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 75212-VinylpyridineHCID 14798Sodium HydroxideHCID 685600921,2,3,4,5,6-Hexahydro-3,9-dimethylazepino[4,5-b]indole

Product 1

HCID 59368249HCID 59368249, compoundYield 35.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

The title compound was prepared by following general procedure 4. To a solution of 3,9-dimethyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole (150 mg, 0.7 mmol) in 50% aq. NaOH solution (7 mL) tetra n-butyl ammonium chloride (9 mg, 0.03 mmol) followed by 2-vinylpyridine (80 mg, 0.77 mmol) was added and the reaction mixture was heated at 80° C. for 14 h. After completion of reaction, the reaction mixture was diluted with water, extracted with ethyl acetate; the organic layer was dried over Na2SO4, and concentrated under reduced pressure. The crude product was purified by reverse phase chromatography to afford 80 mg of 3,9-dimethyl-6-(2-(pyridin-2-yl)ethyl)-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole as the TFA salt.

Workup

  1. customThe title compound was prepared
  2. additionwas added
  3. customAfter completion of reaction
  4. extractionextracted with ethyl acetate
  5. dry with materialthe organic layer was dried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by reverse phase chromatography

Sources & evidence

ORD record
ord-2c370214ec614da4b46e3b1991c4004a
Source dataset
uspto-grants-2013_10
Patent number
US08569287B2

Reaction notes

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