Methyl iodide → HCID 86605588, compound

HRID 2245342Notes

Reaction equation

HRID 2245342 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH:10]([C:15]2[CH:20]=[CH:19][CH:18]=CC=2C)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:22][I:23]>CC(C)=O>[I-:23].[CH2:1]([N+:8]1([CH3:22])[CH2:13][CH2:12][C:11](=[O:14])[CH:10]([CH2:15][CH2:20][CH2:19][CH3:18])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 18001144HCID 18001144, compound

Product 1

HCID 86605588HCID 86605588, compoundYield 61.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 1-benzyl-3-o-tolyl-piperidine-4-one (5165 mg) in acetone (25 ml) was slowly added methyl iodide (3048 mg) at room temperature. The solution was stirred at room temperature over night. A white solid precipitated and was filtered off. The solid was washed four times with 50 ml of acetone and dried under reduced vacuum. The filtrate was evaporated and the residue was stirred with ethyl acetate. The white solid was filtered, washed with ethyl acetate and dried under vacuum. The two solids were combined to yield 1-benzyl-3-butyl-1-methyl-4-oxo-piperidinium iodide as a yellowish solid (4400 mg). MS (ESI): 294.3 (M−I−).

Workup

  1. customat room temperature
  2. customA white solid precipitated
  3. filtrationwas filtered off
  4. washThe solid was washed four times with 50 ml of acetone
  5. customdried under reduced vacuum
  6. customThe filtrate was evaporated
  7. stirringthe residue was stirred with ethyl acetate
  8. filtrationThe white solid was filtered
  9. washwashed with ethyl acetate
  10. customdried under vacuum

Sources & evidence

ORD record
ord-7f40de31d55446a48d2a191f11c2e689
Source dataset
uspto-grants-2010_03
Patent number
US07683079B2

Reaction notes

Loading…