Propane sultone → 3-[(3,4,5-trimethoxyphenyl)methylamino]propane-1-sulfonic acid

HRID 239724

Reaction equation

HRID 239724 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12])[CH2:6][NH2:7].[CH2:15]1[CH2:21][S:18](=[O:20])(=[O:19])[O:17][CH2:16]1>CC(=O)CC>[CH3:14][O:13][C:9]1[CH:8]=[C:5]([CH:4]=[C:3]([O:2][CH3:1])[C:10]=1[O:11][CH3:12])[CH2:6][NH:7][CH2:16][CH2:15][CH2:21][S:18]([OH:20])(=[O:19])=[O:17]

Participants

4

Reactant 2

HCID 14264Propane sultoneHCID 877363,4,5-Trimethoxybenzylamine

Product 1

HCID 112440913-[(3,4,5-trimethoxyphenyl)methylamino]propane-1-sulfonic acid

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

To a solution of 3,4,5-trimethoxybenzylamine (2.2 mL, 12.7 mmol) in 2-butanone (20 mL) was added 1,3-propane sultone (1.66 g, 13.3 mmol). The mixture was stirred at reflux for 2 hours. The reaction mixture was cooled to room temperature. The solid was collected by filtration, washed with acetone (2×25 mL) and dried in vacuo. The product was suspended in 90% Acetone/MeOH (75 mL). The suspension was stirred at reflux for 30 sec., the solid was collected by filtration, and dried in vacuo; affording compound AY, 2.61 g (64%).

Workup

  1. temperatureat reflux for 2 hours
  2. filtrationThe solid was collected by filtration
  3. washwashed with acetone (2×25 mL)
  4. customdried in vacuo
  5. stirringThe suspension was stirred
  6. temperatureat reflux for 30 sec
  7. filtration, the solid was collected by filtration
  8. customdried in vacuo

Sources & evidence

ORD record
ord-535800c29323409091388f40c2a794bb
Source dataset
uspto-grants-2014_02
Patent number
US08642801B2

Linked notes

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