Ethanol → HCID 17777129, compound

HRID 583084Notes

Reaction equation

HRID 583084 reaction equation
[CH3:1][C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]([CH2:12][CH:13]=[CH2:14])[S:4](=[O:16])(=[O:15])[N:3]=1.[BH4-].[Na+].[H-].[Na+].O.[CH2:22](O)C>CN(C)C=O>[CH3:22][N:3]1[CH:2]([CH3:1])[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]([CH2:12][CH:13]=[CH2:14])[S:4]1(=[O:16])=[O:15]

Participants

7

Reactant 5

HCID 702EthanolHCID 962WaterHCID 24758Sodium hydrideHCID 4311764Sodium borohydrideHCID 11345384HCID 11345384, compound

Product 1

HCID 17777129HCID 17777129, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Methyl-1-(prop-2-en-1-yl)-1H-2,1,3-benzothiadiazine-2,2-dioxide(2 g) was dissolved in ethanol(50 ml) and treated with sodium borohydride (350 mg) at room temperature. After 15 minutes, the solvent was removed in vacuo and water added(200 ml). The product was extracted with chloroform(3×100 ml), dried, filtered and evaporated in vacuo to give a solid. This was dissolved in dry dimethylformamide (35 ml) and treated with sodium hydride (350 mg) at room temperature for 30 minutes followed by methyl iodide(600 μl). The reaction was stirred at room temperature for 1 hour, poured into water(250 ml), extracted with ether (3×75 ml), dried, filtered and the solvent removed to give 3,4-dihydro-3,4-dimethyl-1-(prop-2-en-1-yl)-1H-2,1,3-benzothiadiazine-2,2-dioxide. This product was dissolved in dioxan (25 ml) and treated with osmium tetroxide (2 crystals) and sodium periodate(3.6 g) in water(25 ml) and stirred at room temperature overnight. Water was added(100 ml) and the product extracted with ether(3×100 ml), dried, filtered and the solvent removed to give an oil. This was dissolved in methanol(50 ml) and treated with 4-(6-fluoroindol-3-yl)-1,2,5,6-tetrahydro-1-pyridine (1.2 g) at room temperature overnight in the presence of acetic acid(1 ml) and 3A molecular sieves(2 g). Sodium cyanoborohydride(1 g) was then added and the reaction stirred for 4 hours. A further quantity of acetic acid (1 ml) and sodium cyanoborohydride(1 g) were added and stirred at room temperature for 18 hours. Saturated sodium bicarbonate (250 ml) was added and the mixture extracted with ethyl acetate (3×100 ml). After drying, filtering and removal of solvent, flash chromatography on the residue eluting with chloroform/ethyl acetate to ethyl acetate gave product, 3,4-dihydro-1-{2-[4-(6-fluoroindol-3-yl)-1,2,5,6-tetrahydro-1-pyridyl]-1-ethyl}-3,4-dimethyl-1H-2,1,3-benzothiadiazine-2,2-dioxide, m.p.105-108° C.

Workup

  1. customthe solvent was removed in vacuo and water
  2. additionadded(200 ml)
  3. extractionThe product was extracted with chloroform(3×100 ml)
  4. customdried
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto give a solid
  8. extractionextracted with ether (3×75 ml)
  9. customdried
  10. filtrationfiltered
  11. customthe solvent removed

Sources & evidence

ORD record
ord-5aae366a6d884b7aac75ad3907540433
Source dataset
uspto-grants-1999_07
Patent number
US05929072

Reaction notes

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