Propane sultone → 1-Propanesulfonic acid, 3-[(1-methyl-1-phenylethyl)amino]-

HRID 239741Notes

Reaction equation

HRID 239741 reaction equation
[C:1]([NH2:10])([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[CH2:11]1[CH2:17][S:14](=[O:16])(=[O:15])[O:13][CH2:12]1>O1CCCC1>[C:1]([NH:10][CH2:12][CH2:11][CH2:17][S:14]([OH:16])(=[O:15])=[O:13])([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 14264Propane sultoneHCID 68509Cumylamine

Product 1

HCID 113912421-Propanesulfonic acid, 3-[(1-methyl-1-phenylethyl)amino]-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of cumylamine (10.5 g, 78 mmol) in tetrahydrofuran (75 mL) was slowly added a solution of 1,3-propane sultone (9.2 g, 74 mmol) in THF (20 mL). The mixture was stirred at reflux for 4 h. The reaction mixture was cooled to room temperature. The solid was collected by filtration, and washed with THF (2×35 mL). The solid was suspended in EtOH (80 mL). The suspension was stirred at reflux for 15 minutes. The solid product was collected by filtration, washed with EtOH (35 mL) and acetone (35 mL). The resulting solid was dried in vacuo, affording compound DM (5.6 g, 30%). 1H NMR (D2O, 500 MHz) 8 ppm 7.41 (m, 5H), 2.74 (m, 4H), 1.88 (m, 2H), 1.66 (s, 6H). 13C NMR (D2O, 125 MHz) 8 ppm 138.36, 129.44, 129.41, 126.52, 61.56, 48.04, 41.21, 24.80, 21.81. ES-MS 256 (M−1).

Workup

  1. temperatureat reflux for 4 h
  2. filtrationThe solid was collected by filtration
  3. washwashed with THF (2×35 mL)
  4. stirringThe suspension was stirred
  5. temperatureat reflux for 15 minutes
  6. filtrationThe solid product was collected by filtration
  7. washwashed with EtOH (35 mL) and acetone (35 mL)
  8. customThe resulting solid was dried in vacuo
  9. customaffording compound DM (5.6 g, 30%)

Sources & evidence

ORD record
ord-7d797dea8f92471488a016855e47fa87
Source dataset
uspto-grants-2014_02
Patent number
US08642801B2

Reaction notes

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