Hydrogen Peroxide → HCID 11709404, compound

HRID 2060064Notes

Reaction equation

HRID 2060064 reaction equation
Cl.[CH3:2][N:3]([CH3:22])[CH2:4][C:5]1[CH2:11][CH2:10][S:9][C:8]2[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=2[C:6]=1[C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1.OO.C(OCC)(=[O:27])C.[OH-].[Na+]>C(O)(=O)C>[CH3:2][N:3]([CH3:22])[CH2:4][C:5]1[CH2:11][CH2:10][S:9](=[O:27])[C:8]2[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=2[C:6]=1[C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 69452599HCID 69452599, compound

Product 1

HCID 11709404HCID 11709404, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

0.5 g of dimethyl-(5-pyridin-3-yl-2,3-dihydro-benzo[b]thiepin-4-ylmethyl)-amine hydrochloride was dissolved in 2.5 ml of glacial acetic acid; 0.29 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 three times with ethyl acetate; the combined organic phases were dried over magnesium sulfate, filtered and concentrated in vacuo. 0.35 g of crude product was obtained and was purified by means of preparative HPLC (Hypercarb 5 μm 120×4 mm, 0.5 ml/min., acetonitrile/water (v/v=70:30+0.1% diethylamine). After filtration through a MF-Millipore-MCE membrane (mixed cellulose esters; 0.45 μm), 0.102 g of dimethyl-(1-oxo-5-pyridin-3-yl-2,3-dihydro-1H-1λ4-benzo[b]thiepin-4-ylmethyl)-amine was obtained and was dissolved in 3 ml of 2-acetone p.a. and converted into the corresponding hydrochloride with about 0.003 ml of water and about 0.041 ml of chlorotrimethylsilane, while cooling with ice; the hydrochloride was dried in vacuo (about 50 mbar) (yield 0.1 g).

Workup

  1. stirringstirring
  2. temperaturewhile cooling with ice
  3. extractionextracted three times with ethyl acetate
  4. dry with materialthe combined organic phases were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. custom0.35 g of crude product was obtained
  8. customwas purified by means of preparative HPLC (Hypercarb 5 μm 120×4 mm, 0.5 ml/min., acetonitrile/water (v/v=70:30+0.1% diethylamine)
  9. filtrationAfter filtration
  10. additionthrough a MF-Millipore-MCE membrane (mixed cellulose esters; 0.45 μm)

Sources & evidence

ORD record
ord-7d61608804b24fa9bb19ba8348df943f
Source dataset
uspto-grants-2012_10
Patent number
US08278338B2

Reaction notes

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