Propane sultone → 3-[(3-Methylpentan-3-yl)amino]propane-1-sulfonic acid

HRID 239809Notes

Reaction equation

HRID 239809 reaction equation
[CH2:1]1[CH2:7][S:4](=[O:6])(=[O:5])[O:3][CH2:2]1.[CH3:8][C:9]([NH2:14])([CH2:12][CH3:13])[CH2:10][CH3:11]>CC(=O)CC.C1(C)C=CC=CC=1>[CH2:10]([C:9]([NH:14][CH2:2][CH2:1][CH2:7][S:4]([OH:3])(=[O:6])=[O:5])([CH3:8])[CH2:12][CH3:13])[CH3:11]

Participants

5

Reactant 2

HCID 14264Propane sultoneHCID 43396263-Methylpentan-3-amine

Product 1

HCID 160358463-[(3-Methylpentan-3-yl)amino]propane-1-sulfonic acid

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

A solution of 1,3-propanesultone (2.5 g, 20 mmol) in 2-butanone (10 mL) was added to a solution of 3-methyl-3-ethyl-3-propylamine in toluene (total volume: 30 mL). The mixture was heated to reflux for 5 hours then was cooled to room temperature. The solid was collected by suction-filtration and rinsed with acetone (2×5 mL). The solid was dried overnight at 45° C. in the vacuum oven. The title compound was obtained as a fine white solid (3.63 g, 16.3 mmol, 33% overall yield). 1H NMR (500 MHz, DMSO-d6) δ 0.79 (t, J=7.3 Hz, 6H), 1.15 (s, 3H), 1.53-1.59 (m, 4H), 1.97-2.00 (m, 2H), 2.89 (t, J=7.1 Hz, 2H), 3.03 (t, J=7.6 Hz, 2H); 13C NMR (125 MHz, DMSO-d6) δ 6.8, 20.2, 21.9, 27.7, 39.7, 48.2, 63.3 ES-MS 224; (M+H)

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 5 hours
  3. filtrationThe solid was collected by suction-filtration
  4. washrinsed with acetone (2×5 mL)
  5. customThe solid was dried overnight at 45° C. in the vacuum oven

Sources & evidence

ORD record
ord-0528ba1eb40441da9965983ae441f907
Source dataset
uspto-grants-2014_02
Patent number
US08642801B2

Reaction notes

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