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

HRID 239735

Reaction equation

HRID 239735 reaction equation
[C:1]([NH2:6])([CH2:4][CH3:5])([CH3:3])[CH3:2].[CH2:7]1[CH2:13][S:10](=[O:12])(=[O:11])[O:9][CH2:8]1>O1CCCC1>[C:1]([NH:6][CH2:8][CH2:7][CH2:13][S:10]([OH:12])(=[O:11])=[O:9])([CH2:4][CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 14264Propane sultoneHCID 689862-Butanamine, 2-methyl-

Product 1

HCID 114471401-Propanesulfonic acid, 3-[(1,1-dimethylpropyl)amino]-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-amylamine (2.0 g, 23.3 mmol) in tetrahydrofuran (15 mL) was added 1,3-propane sultone (2.76 g, 22.2 mmol). The solution was stirred at reflux for 2 hours. The reaction mixture was cooled to room temperature. The solid product was collected by filtration, washed with acetone (2×25 mL), and dried in vacuo, to afford compound DG (3.3 g, 73%): 1H NMR (D2O, 500 MHz) 8 ppm 3.04 (t, 2H, J=7.8 Hz), 2.89 (t, 2H, J=7.8 Hz), 2.87 (t, 2H, J=7.3 Hz), 1.97 (m, 2H), 1.55 (m, 2H), 1.18 (s, 6H), 0.82 (t, 6H, J=7.3 Hz). 13C NMR (D2O, 125 MHz) 8 ppm 60.42, 48.17, 39.88, 30.81, 22.23, 21.98, 7.25. ES-MS 208 (M−1).

Workup

  1. temperatureat reflux for 2 hours
  2. filtrationThe solid product was collected by filtration
  3. washwashed with acetone (2×25 mL)
  4. customdried in vacuo
  5. customto afford compound DG (3.3 g, 73%)

Sources & evidence

ORD record
ord-11d0717c84cd4941afbcf62f62953065
Source dataset
uspto-grants-2014_02
Patent number
US08642801B2

Linked notes

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