Propane sultone → 4-Phenyl-1-(3'-sulfopropyl)-1,2,3,6 tetrahydropyridine

HRID 1817253Notes

Reaction equation

HRID 1817253 reaction equation
[C:1]1([C:7]2[CH2:8][CH2:9][NH:10][CH2:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:13]1[CH2:19][S:16](=[O:18])(=[O:17])[O:15][CH2:14]1>CC(C)=O>[C:1]1([C:7]2[CH2:12][CH2:11][N:10]([CH2:14][CH2:13][CH2:19][S:16]([OH:18])(=[O:17])=[O:15])[CH2:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 14264Propane sultoneHCID 825531,2,3,6-Tetrahydro-4-phenylpyridine

Product 1

HCID 98179064-Phenyl-1-(3'-sulfopropyl)-1,2,3,6 tetrahydropyridine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 4-phenyl-1,2,3,6-tetrahydropyridine (1.95 g, 12.2 mmol) in acetone (20 mL) was added 1,3-propane sultone (1.66 g, 13.5 mmol). The mixture was stirred at reflux for 2 h. The resulting suspension 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 50% MeOH/acetone (75 mL). The suspension was stirred at reflux for 5 min. The solid material was filtered and washed with acetone (2×25 μL). This allowed the isolation of compound O, 1.74 g (51%).

Workup

  1. temperatureat reflux for 2 h
  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 5 min
  7. filtrationThe solid material was filtered
  8. washwashed with acetone (2×25 μL)

Sources & evidence

ORD record
ord-24399d17ca30467093650227a8a82ff9
Source dataset
uspto-grants-2009_10
Patent number
US07598269B2

Reaction notes

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