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

HRID 239743

Reaction equation

HRID 239743 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-af6c9691b0c443de8ca4aaaef90cde59
Source dataset
uspto-grants-2014_02
Patent number
US08642801B2

Linked notes

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