Propane sultone → Agn-PC-00FU26

HRID 239715Notes

Reaction equation

HRID 239715 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:9][CH2:10][NH:11][CH2:12][CH:13]=2)=[CH:4][CH:3]=1.[CH2:14]1[CH2:20][S:17](=[O:19])(=[O:18])[O:16][CH2:15]1>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][CH2:12][N:11]([CH2:15][CH2:14][CH2:20][S:17]([OH:19])(=[O:18])=[O:16])[CH2:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14264Propane sultoneHCID 1857174-(4-Chlorophenyl)-1,2,3,6-tetrahydropyridine

Product 1

HCID 11771457Agn-PC-00FU26

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 4-(4-chlorophenyl)-1,2,3,6-tetrahydropyridine (2.07 g, 10.7 mmol) in acetone (25 mL) was added 1,3-propane sultone (1.41 g, 11.8 mmol). The mixture was stirred at reflux for 2 h. The reaction mixture was cooled to room temperature. The solid was collected by filtration, washed with acetone (2×20 mL) and dried in vacuo. The product was suspended in 50% MeOH/acetone (75 mL). The suspension was stirres at reflux for 5 minutes before 25 mL of cold acetone was added. The solid material was filtered and washed with acetone (2×25 mL). This allowed the isolation of compound J, 1.48 g (44%).

Workup

  1. temperatureat reflux for 2 h
  2. filtrationThe solid was collected by filtration
  3. washwashed with acetone (2×20 mL)
  4. customdried in vacuo
  5. temperatureat reflux for 5 minutes before 25 mL of cold acetone
  6. additionwas added
  7. filtrationThe solid material was filtered
  8. washwashed with acetone (2×25 mL)

Sources & evidence

ORD record
ord-ebe39febe7294c32887a7cc898bdaca8
Source dataset
uspto-grants-2014_02
Patent number
US08642801B2

Reaction notes

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