3-Pentanamine → 1-Propanesulfonic acid, 3-[(1-ethylpropyl)amino]-

HRID 239734Notes

Reaction equation

HRID 239734 reaction equation
[CH2:1]([CH:3]([NH2:6])[CH2:4][CH3:5])[CH3:2].[CH2:7]1[CH2:13][S:10](=[O:12])(=[O:11])[O:9][CH2:8]1>O1CCCC1>[CH3:2][CH2:1][CH:3]([NH:6][CH2:8][CH2:7][CH2:13][S:10]([OH:12])(=[O:11])=[O:9])[CH2:4][CH3:5]

Participants

4

Reactant 2

HCID 120193-PentanamineHCID 14264Propane sultone

Product 1

HCID 114471391-Propanesulfonic acid, 3-[(1-ethylpropyl)amino]-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1-ethylpropylamine (10.0 g, 115 mmol) in tetrahydrofuran (80 mL) was added a solution of 1,3-propane sultone (13.7 g, 110 mmol) in 20 mL of THF. 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 (2×50 mL), and dried in vacuo., to afford compound DD (18.1, 80%): 1H NMR (D2O, 500 MHz) 8 ppm 3.08 (t, 2H, J=7.3 Hz), 3.01 (m, 1H), 2.87 (t, 2H, J=7.3 Hz) 2.00 (m, 2H), 1.59 (m, 4H), 0.82 (t, 6H, J=7.3 Hz). 13C NMR (D2O, 125 MHz) 8 ppm 60.87, 48.14, 43.68, 21.81. 21.60, 8.25. ES-MS 208 (M−1).

Workup

  1. temperatureat reflux for 2 hours
  2. filtrationThe solid product was collected by filtration
  3. washwashed with acetone (2×50 mL)
  4. customdried in vacuo
  5. custom, to afford compound DD (18.1, 80%)

Sources & evidence

ORD record
ord-3d7516457fca4c658a54b1f0cb01bf1c
Source dataset
uspto-grants-2014_02
Patent number
US08642801B2

Reaction notes

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