4-Methyl-N-(2-oxo-3-azepanyl)benzenesulfonamide → N-(Azepan-3-yl)-4-methylbenzenesulfonamide

HRID 458620Notes

Reaction equation

HRID 458620 reaction equation
O=[C:2]1[CH:8]([NH:9][S:10]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)(=[O:12])=[O:11])[CH2:7][CH2:6][CH2:5][CH2:4][NH:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[NH:3]1[CH2:4][CH2:5][CH2:6][CH2:7][CH:8]([NH:9][S:10]([C:13]2[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][CH:18]=2)(=[O:11])=[O:12])[CH2:2]1

Participants

4

Reactant 2

HCID 38035924-Methyl-N-(2-oxo-3-azepanyl)benzenesulfonamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 22508595N-(Azepan-3-yl)-4-methylbenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(2-Oxoazepan-3-yl)-4-methylbenzenesulfonamide (6A) (4.24 g, 15 mmol) was dissolved in 250 ml of dry THF under a nitrogen atmosphere, and lithium aluminium hydride (1.11 g, 30 mmol) was added slowly. The reaction was heated to reflux for 20 hours and then quenched with water until the effervescence ceased. Solid potassium carbonate was added until a white suspension appeared, and the mixture was allowed to stir for half an hour. The suspension was filtered through celite, which was washed with 3×50 ml of EtOAc. The solvents were evaporated and the residue was dissolved in 100 ml of EtOAc and 100 ml of water. The layers were separated and the aqueous layer was extracted with 2×100 ml of EtOAc. The combined organic layer was washed with brine, dried over sodium sulphate, and evaporated to give compound (6B) as an oil.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 20 hours
  3. customquenched with water until the effervescence
  4. additionSolid potassium carbonate was added until a white suspension
  5. filtrationThe suspension was filtered through celite, which
  6. washwas washed with 3×50 ml of EtOAc
  7. customThe solvents were evaporated
  8. dissolutionthe residue was dissolved in 100 ml of EtOAc
  9. customThe layers were separated
  10. extractionthe aqueous layer was extracted with 2×100 ml of EtOAc
  11. washThe combined organic layer was washed with brine
  12. dry with materialdried over sodium sulphate
  13. customevaporated

Sources & evidence

ORD record
ord-eec6c5143ef04531842b22d66ca66e0e
Source dataset
uspto-grants-2007_03
Patent number
US07192952B2

Reaction notes

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