Propane sultone → HCID 11358219, compound

HRID 239731Notes

Reaction equation

HRID 239731 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH2:6][NH2:7].[CH2:13]1[CH2:19][S:16](=[O:18])(=[O:17])[O:15][CH2:14]1>CC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH2:6][NH:7][CH2:14][CH2:13][CH2:19][S:16]([OH:18])(=[O:17])=[O:15]

Participants

4

Reactant 2

HCID 14264Propane sultoneHCID 79832Veratrylamine

Product 1

HCID 11358219HCID 11358219, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 3,4-dimethoxybenzylamine (2.2 mL, 15.0 mmol) in acetone (20 mL) was added 1,3-propane sultone (1.97 g, 15.8 mmol). The mixture was stirred at reflux for 2 hours. The reaction mixture was cooled to room temperature. The solid material was collected by filtration, washed with acetone (2×25 mL) and dried in vacuo. The crude product was suspended in 90% acetone/MeOH (75 mL). The suspension was stirred at reflux for 30 sec., the solid material was collected by filtration, and dried in vacuo. Compound S (1.84 g, 43%) was isolated as a white solid. 1H NMR (D2O, 500 MHz) 8 ppm 6.96 (m, 3H), 4.06 (s, 2H), 3.74 (s, 6H), 3.07 (t, 1H, J=7.8 Hz), 2.86 (t, 1H, J=7.8 Hz), 2.01 (m, 2H). 13C NMR (D2O, 125 MHz) 8 ppm 149.23, 148.50, 123.63, 123.37, 55.90, 55.86, 50.96, 48.06, 45.62, 21.39. ES-MS 290 (M+1).

Workup

  1. temperatureat reflux for 2 hours
  2. filtrationThe solid material 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 material was collected by filtration
  8. customdried in vacuo

Sources & evidence

ORD record
ord-9d325a0039994dc2a5e929adc3f4ed0e
Source dataset
uspto-grants-2014_02
Patent number
US08642801B2

Reaction notes

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