1,2-Dimethylpropylamine → 1-Propanesulfonic acid, 3-[(1,2-dimethylpropyl)amino]-

HRID 2219752Notes

Reaction equation

HRID 2219752 reaction equation
[CH3:1][CH:2]([NH2:6])[CH:3]([CH3:5])[CH3:4].[CH2:7]1[CH2:13][S:10](=[O:12])(=[O:11])[O:9][CH2:8]1>O1CCCC1>[CH3:1][CH:2]([NH:6][CH2:8][CH2:7][CH2:13][S:10]([OH:12])(=[O:11])=[O:9])[CH:3]([CH3:5])[CH3:4]

Participants

4

Reactant 2

HCID 117311,2-DimethylpropylamineHCID 14264Propane sultone

Product 1

HCID 114812161-Propanesulfonic acid, 3-[(1,2-dimethylpropyl)amino]-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1,2-dimethylpropylamine (10.0 g, 115 mmol) in tetrahydrofuran (80 mL) was slowly added a solution of 1,3-propane sultone (13.7 g, 110 mmol) in THF (20 mL). 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 THF (50 mL) and EtOH (50 mL). The resulting solid was dried in vacuo, to afford compound DQ (17.5 g, 76%). 1H NMR (D2O, 500 MHz) δ ppm 3.07 (m, 3H), 2.88 (t, 2H, J=7.3 Hz), 1.97 (m, 3H) 1.10 (d, 3H, J=6.8 Hz), 0.85 (d, 3H, J=6.8 Hz), 0.81 (d, 3H, J=6.8 Hz). 13C NMR (D2O, 125 MHz) δ ppm 59.79, 48.19, 44.18, 29.72, 21.51, 18.44, 15.02, 10.71. ES-MS 232 (M+Na).

Workup

  1. temperatureat reflux for 2 hours
  2. filtrationThe solid product was collected by filtration
  3. washwashed with THF (50 mL) and EtOH (50 mL)
  4. customThe resulting solid was dried in vacuo
  5. customto afford compound DQ (17.5 g, 76%)

Sources & evidence

ORD record
ord-03a15fd983664a8f8405420cbae9ea87
Source dataset
uspto-grants-2008_08
Patent number
US07414076B2

Reaction notes

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