Propane sultone → HCID 11188102, compound

HRID 239713Notes

Reaction equation

HRID 239713 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:14])[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH2:15]1[CH2:21][S:18](=[O:20])(=[O:19])[O:17][CH2:16]1>CO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:14])[CH2:9][CH2:10][N:11]([CH2:16][CH2:15][CH2:21][S:18]([OH:20])(=[O:19])=[O:17])[CH2:12][CH2:13]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14264Propane sultoneHCID 939114-(4-Bromophenyl)-4-hydroxypiperidine

Product 1

HCID 11188102HCID 11188102, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-(4-bromophenyl)-4-piperidinol (2.51 g, 9.8 mmol) in MeOH (25 mL) was added 1,3-propane sultone (1.28 g, 10.7 mmol). The mixture was stirred at reflux for 2 h. Only a small amount of compound precipitated. The resulting suspension was cooled to room temperature with stirring and a solution of 50% MeOH/Acetone was added to precipitate a maximum of compound. The solid was collected by filtration, washed with 50% MeOH/Acetone (2×25 mL) and dried in vacuo. This allowed the isolation of compound G, 2.11 g (57%).

Workup

  1. temperatureat reflux for 2 h
  2. customOnly a small amount of compound precipitated
  3. stirringwith stirring
  4. additiona solution of 50% MeOH/Acetone was added
  5. customto precipitate a maximum of compound
  6. filtrationThe solid was collected by filtration
  7. washwashed with 50% MeOH/Acetone (2×25 mL)
  8. customdried in vacuo

Sources & evidence

ORD record
ord-6923bc59f37540a5b095ca3c496b31d0
Source dataset
uspto-grants-2014_02
Patent number
US08642801B2

Reaction notes

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