Propane sultone → Agn-PC-004N6H

HRID 239712Notes

Reaction equation

HRID 239712 reaction equation
[F: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>[F: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 1977484-(4-Fluorophenyl)-1,2,3,6-tetrahydropyridine

Product 1

HCID 11220282Agn-PC-004N6H

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 4-(4-fluorophenyl)-1,2,3,6-tetrahydropyridine (1.96 g, 13.7 mmol) in acetone (30 mL) was added 1,3-propane sultone (1.74 g, 14.5 mmol). The mixture was stirred at reflux overnight. Only a small amount of compound precipitated. The resulting suspension was cooled to room temperature with stiffing and a larger amount of solid precipitated. The suspension was heated with the addition of a small amount of MeOH until complete dissolution of the solid. The resulting solution was stirred at reflux for a few minutes and was cooled to room temperature with stiffing. The solid was collected by filtration, washed with MeOH and dried in vacuo. This allowed the isolation of compound F, 1.33 g (32%).

Workup

  1. temperatureat reflux overnight
  2. customOnly a small amount of compound precipitated
  3. customa larger amount of solid precipitated
  4. temperatureThe suspension was heated with the addition of a small amount of MeOH until complete dissolution of the solid
  5. stirringThe resulting solution was stirred
  6. temperatureat reflux for a few minutes
  7. temperaturewas cooled to room temperature with stiffing
  8. filtrationThe solid was collected by filtration
  9. washwashed with MeOH
  10. customdried in vacuo

Sources & evidence

ORD record
ord-d122c7acce3345128715b12f1c374a71
Source dataset
uspto-grants-2014_02
Patent number
US08642801B2

Reaction notes

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