Acetone → 4-(Octylamino)butane-1-sulfonic acid

HRID 239799Notes

Reaction equation

HRID 239799 reaction equation
[CH2:1]([NH2:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH2:10]1[CH2:17][O:16][S:13](=[O:15])(=[O:14])[CH2:12][CH2:11]1.CC(C)=O>O1CCCC1.CCO>[CH2:1]([NH:9][CH2:17][CH2:10][CH2:11][CH2:12][S:13]([OH:16])(=[O:15])=[O:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 3

HCID 180AcetoneHCID 8143OctylamineHCID 154111,4-Butane sultone

Product 1

HCID 589318684-(Octylamino)butane-1-sulfonic acidYield 31%

Reagents, catalysts & solvents 2

HCID 702EthanolCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of octylamine (2.20 g, 17.0 mmol) in tetrahydrofuran (11 mL) was added 1,4-butane sultone (2.30 g, 16.2 mmol). The solution was heated to reflux for 5 hours. The reaction was cooled to room temperature. The product formed a gel. A few drops of EtOH were added to dissolve the product. The solution was poured in a large excess of acetone (25 mL). After 5 minutes, a white solid precipitated. The solid was collected by filtration and dried in vacuo. The product was dissolved in EtOH and Dowex 50×8 resin (pre-washed, 6 g) was added to the solution. The suspension was stirred for 15 minutes and the resin was filtered. The filtrate was evaporated under educed pressure and the product was dried in vacuo. Yield: 31%. 1H NMR (DMSO, 500 MHz) δ ppm 8.24 (s (broad), 1H), 2.85 (m, 4H), 2.45 (m, 2H), 1.64 (m, 4H), 1.61 (m, 2H), 1.25 (m, 10H), (m, 2H), 0.85 (t, 3H, J=6.8 Hz). 13C (DMSO, 125 MHz) δ ppm 51.22, 47.54, 47.38, 31.82, 29.14, 26.59, 26.13, 25.51, 22.95, 22.75, 14.64. ES-MS 266 (M+1).

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 5 hours
  3. customThe product formed a gel
  4. dissolutionto dissolve the product
  5. customa white solid precipitated
  6. filtrationThe solid was collected by filtration
  7. customdried in vacuo
  8. dissolutionThe product was dissolved in EtOH
  9. washDowex 50×8 resin (pre-washed, 6 g)
  10. additionwas added to the solution
  11. filtrationthe resin was filtered
  12. customThe filtrate was evaporated under educed pressure
  13. customthe product was dried in vacuo

Sources & evidence

ORD record
ord-ad0584cfe4c742b5bcb8488aff9a766f
Source dataset
uspto-grants-2014_02
Patent number
US08642801B2

Reaction notes

Loading…