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

HRID 1070698

Reaction equation

HRID 1070698 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 hours. 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-c9f3ab24e3d249ab9e8e55d965ecc83a
Source dataset
uspto-grants-2005_06
Patent number
US06903117B2

Linked notes

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