Propane sultone → 1-Propanesulfonic acid, 3-[(2,3-dimethylcyclohexyl)amino]-

HRID 239739Notes

Reaction equation

HRID 239739 reaction equation
[CH3:1][CH:2]1[CH:7]([CH3:8])[CH2:6][CH2:5][CH2:4][CH:3]1[NH2:9].[CH2:10]1[CH2:16][S:13](=[O:15])(=[O:14])[O:12][CH2:11]1>O1CCCC1>[CH3:1][CH:2]1[CH:7]([CH3:8])[CH2:6][CH2:5][CH2:4][CH:3]1[NH:9][CH2:11][CH2:10][CH2:16][S:13]([OH:15])(=[O:14])=[O:12]

Participants

4

Reactant 2

HCID 14264Propane sultoneHCID 1235072,3-Dimethylcyclohexylamine

Product 1

HCID 112304261-Propanesulfonic acid, 3-[(2,3-dimethylcyclohexyl)amino]-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2,3-dimethylcyclohexylamine (10.0 g, 79.0 mmol) in tetrahydrofuran (60 mL) was slowly added a solution of 1,3-propane sultone (9.3 g, 75.0 mmol) in THF (20 mL). The solution was stirred at reflux for 2 hours. The reaction mixture was cooled to room temperature. The solid was collected by filtration, washed with THF (50 mL) and acetone (50 mL). The solid was dissolved in 25% EtOH/water (150 mL), and treated with Dowex 50WX8 resin (15 g). The suspension stirred at room temperature for 5 minutes. The resin was removed by filtration. The filtrate was concentrated to dryness under reduced pressure; and the solid residue was suspended in acetone (100 mL). The solid material was collected by filtration, and dried in vacuo; affording compound DK (7.4 g, 43%). 1H NMR (D2O, 500 MHz) 8 ppm 3.29 (m, 0.5H), 3.09 (m, 2H), 2.88 (t, 2H, J=7.3 Hz), 2.80 (m, 0.5H), 1.99 (m, 3H), 1.40 (m, 7H), 0.81 (m, 6H). 13C NMR (D2O, 125 MHz) 8 ppm 62.85, 61.56, 59.88, 58.22, 48.26, 48.15, 44.29, 43.84, 43.59, 42.65, 42.01, 41.03, 37.34, 36.12, 34.73, 34.45, 33.88, 33.64, 29.39, 28.00, 26.50, 24.25, 24.02, 23.64, 22.42, 21.55, 21.45, 21.35, 19.38, 19.13, 18.82, 18.40, 14.38, 13.39, 4.59. ES-MS 248 (M−1).

Workup

  1. temperatureat reflux for 2 hours
  2. filtrationThe solid was collected by filtration
  3. washwashed with THF (50 mL) and acetone (50 mL)
  4. dissolutionThe solid was dissolved in 25% EtOH/water (150 mL)
  5. additiontreated with Dowex 50WX8 resin (15 g)
  6. stirringThe suspension stirred at room temperature for 5 minutes
  7. customThe resin was removed by filtration
  8. concentrationThe filtrate was concentrated to dryness under reduced pressure
  9. filtrationThe solid material was collected by filtration
  10. customdried in vacuo

Sources & evidence

ORD record
ord-6cf2ac762d7c4fc3ab0e7704b415a66d
Source dataset
uspto-grants-2014_02
Patent number
US08642801B2

Reaction notes

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