Methyl iodide → 1,2,2,6,6-Pentamethyl-4-piperidone hydroiodide

HRID 377366

Reaction equation

HRID 377366 reaction equation
O.[CH3:2][C:3]1([CH3:12])[CH2:8][C:7](=[O:9])[CH2:6][C:5]([CH3:11])([CH3:10])[NH:4]1.[CH3:13][I:14]>C(O)(C)C>[IH:14].[CH3:13][N:4]1[C:5]([CH3:11])([CH3:10])[CH2:6][C:7](=[O:9])[CH2:8][C:3]1([CH3:12])[CH3:2]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 223976024-Piperidinone, 2,2,6,6-tetramethyl-, monohydrate

Product 1

HCID 223975731,2,2,6,6-Pentamethyl-4-piperidone hydroiodideYield 46%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 2,2,6,6-tetramethyl-4-piperidone monohydrate (40 g, 23.1 mmol) and methyl iodide (98.31 g, 69.3 mmol) in isopropyl alcohol (25 mL) was stirred at RT for 48 h. The resulting suspension was filtered, the solid residue was dried and recrystallized from MeOH. After filtration and repeated washings with MeOH the solid was dried giving pure title compound (31.6 g, 10.6 mmol, yield 46.0%) as pale brown crystals.

Workup

  1. filtrationThe resulting suspension was filtered
  2. customthe solid residue was dried
  3. customrecrystallized from MeOH
  4. filtrationAfter filtration
  5. washwashings with MeOH the solid
  6. customwas dried

Sources & evidence

ORD record
ord-eae7e283f1c043a3a0d4c9e0ca3c482b
Source dataset
uspto-grants-2000_02
Patent number
US06025390

Linked notes

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