Hydrogen Peroxide → HCID 11709404, compound

HRID 2060065Notes

Reaction equation

HRID 2060065 reaction equation
Cl.[CH3:2][N:3]([CH2:5][CH:6]1[CH2:12][CH2:11][S:10][C:9]2[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=2[C:7]1([C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)O)[CH3:4].OO.C(OCC)(=[O:28])C.[OH-].[Na+]>C(O)(=O)C>[CH3:2][N:3]([CH3:4])[CH2:5][C:6]1[CH2:12][CH2:11][S:10](=[O:28])[C:9]2[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=2[C:7]=1[C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 69449267HCID 69449267, compound

Product 1

HCID 11709404HCID 11709404, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

0.5 g of 4-dimethylaminomethyl-5-pyridin-3-yl-2,3,4,5-tetrahydro-benzo[b]thiepin-5-ol hydrochloride was dissolved in 2.5 ml of glacial acetic acid; about 0.23 ml of 35% hydrogen peroxide solution was added dropwise at room temperature, with stirring, and stirring was continued for 24 hours. The reaction mixture was covered with a layer of ethyl acetate, while cooling with ice, rendered alkaline with 32% sodium hydroxide solution and extracted twice with ethyl acetate; the combined organic phases were washed with saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated in vacuo. 0.38 g of crude product was obtained and was chromatographed on silica gel with ethyl acetate/25% ammonia solution (v/v=98:2). 0.15 g of a mixed fraction and 0.13 g of dimethyl-(1-oxo-5-pyridin-3-yl-2,3-dihydro-1H-1λ4-benzo[b]thiepin-4-ylmethyl)-amine were obtained. The latter was dissolved in 6 ml of 2-acetone p.a. and converted into the corresponding hydrochloride with about 0.004 ml of water and about 0.043 ml of chlorotrimethylsilane, while cooling with ice; the hydrochloride was dried in vacuo (about 50 mbar) (yield 0.09 g of white solid).

Workup

  1. stirringstirring
  2. temperaturewhile cooling with ice
  3. extractionextracted twice with ethyl acetate
  4. washthe combined organic phases were washed with saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. custom0.38 g of crude product was obtained
  9. customwas chromatographed on silica gel with ethyl acetate/25% ammonia solution (v/v=98:2)

Sources & evidence

ORD record
ord-b03c8d9d101147da93fe2a1c08acbdd7
Source dataset
uspto-grants-2012_10
Patent number
US08278338B2

Reaction notes

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