Methyl iodide → HCID 22479032, compound

HRID 2086900Notes

Reaction equation

HRID 2086900 reaction equation
[CH3:1][N:2]([CH3:15])[CH2:3][CH:4]([C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)[C:5](=[O:7])[CH3:6].[I:16][CH3:17]>CCOC(C)=O>[I-:16].[CH3:15][N+:2]([CH3:17])([CH3:1])[CH2:3][CH:4]([C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)[C:5](=[O:7])[CH3:6]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 22479028HCID 22479028, compound

Product 1

HCID 22479032HCID 22479032, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-methylphenylacetone (3.01 g), paraformaldehyde (0.489 g) and dimethylamine hydrochloride (1.49 g) in MeOH (2 ml) is stirred under reflux for 3 h. The reaction mixture is diluted with 20 ml of water and the product is extracted with two portions of ether. After addition of 1 M aqueous NaOH solution, the aqueous layer is extracted with two more portions of ether. The combined organic layers are dried (Na2SO4) and the solvent is evaporated to obtain 4-dimethylamino-3-p-tolyl-butan-2-one (compound of formula VI) as a yellowish liquid, MS (ISP) 206.2 (M+H)+. 4-Dimethylamino-3-p-tolyl-butan-2-one is dissolved in AcOEt (17 ml) and iodomethane (1.46) is added. After 1 h the formed solid is collected by filtration, washed with AcOEt and dried on the vacuum. 2.61 g of trimethyl-(3-oxo-2-p-tolyl-butyl)-ammonium iodide are obtained as an off-white solid, MS (ISP) 220.3 M+.

Workup

  1. filtrationAfter 1 h the formed solid is collected by filtration
  2. washwashed with AcOEt
  3. customdried on the vacuum

Sources & evidence

ORD record
ord-96a66b7139f843678778f516936c1dcf
Source dataset
uspto-grants-2004_04
Patent number
US06727261B2

Reaction notes

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