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

HRID 239756

Reaction equation

HRID 239756 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 (30 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-fba04da01c524e2c854fc8415d00a1c9
Source dataset
uspto-grants-2014_02
Patent number
US08642801B2

Linked notes

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