Ethyl Acetate → 1-Propanesulfonic acid, 3-[[2-(4-bromophenyl)ethyl]amino]-

HRID 2219765Notes

Reaction equation

HRID 2219765 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][NH2:8])=[CH:4][CH:3]=1.[CH2:11]1[CH2:17][S:14](=[O:16])(=[O:15])[O:13][CH2:12]1.CC(=O)OCC>C(#N)C>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][NH:8][CH2:12][CH2:11][CH2:17][S:14]([OH:16])(=[O:15])=[O:13])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 14264Propane sultoneHCID 533915p-Bromophenethylamine

Product 1

HCID 112557131-Propanesulfonic acid, 3-[[2-(4-bromophenyl)ethyl]amino]-Yield 94%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-Bromophenethylamine (4 g, 20 mmol) and 1,3-propane sultone (2.56 g, 21 mmol) in acetonitrile (390 mL) was heated at reflux for 2.5 hours. The mixture was cooled to room temperature. The solid was collected by filtration, rinsed with acetonitrile (2×5 mL) air-dried for 15 minutes (9.57 g), and further dried for 15 minutes in vacuo (8.02 g). The solid was suspended in ethanol (40 mL) and the suspension was heated at reflux for 1 hour. The mixture was then cooled to room temperature. The solid was collected by suction filtration, rinsed with ethanol (2×5 mL), air-dried for 15 minutes, and further dried in a vacuum oven at 60° C. for 18 hours. Compound EA was obtained as a white solid (6.04 g, 18.8 mmol, 94% yield). 1H NMR (500 MHz, DMSO) δ 1.95 (t, J=6.3 Hz, 3H), 2.63 (t, J=6.1 Hz, 2H), 2.88 (t, J=7.6 Hz, 2H), 3.09 (t, J=6.3 Hz, 2H), 3.15 (t, J=7.8 Hz, 2H), 7.25 (2, J=7.8 Hz, 2H), 7.53 (2, J=7.8 Hz, 2H), 8.63 (br s, 2H). 13C NMR (125 MHz, DMSO) δ 21.8, 31.0, 46.7, 47.2, 48.8, 119.9, 131.0, 131.4, 136.5. ES-MS 324 (M+1).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2.5 hours
  3. filtrationThe solid was collected by filtration
  4. washrinsed with acetonitrile (2×5 mL)
  5. customair-dried for 15 minutes (9.57 g)
  6. customfurther dried for 15 minutes in vacuo (8.02 g)
  7. temperaturethe suspension was heated
  8. temperatureat reflux for 1 hour
  9. temperatureThe mixture was then cooled to room temperature
  10. filtrationThe solid was collected by suction filtration
  11. washrinsed with ethanol (2×5 mL)
  12. customair-dried for 15 minutes
  13. customfurther dried in a vacuum oven at 60° C. for 18 hours

Sources & evidence

ORD record
ord-d1960fde921c4e21b03fd68bf183dc8b
Source dataset
uspto-grants-2008_08
Patent number
US07414076B2

Reaction notes

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