Methyl iodide → HCID 15733061, compound

HRID 486070Notes

Reaction equation

HRID 486070 reaction equation
[CH3:1]I.[Mg].[Cl-].[C:5]1([CH2:11][N+:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([CH3:19])[CH:13]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[Cl-].[NH4+]>CCOCC>[C:5]1([CH2:11][N:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([CH3:19])[CH:13]2[CH3:1])[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 139786171-Benzyl-3,4-dimethylpyridin-1-ium chloride

Product 1

HCID 15733061HCID 15733061, compoundYield 88.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

A solution of methyl iodide (112 mL, 1.8 mole) in ether (225 mL) was added dropwise to a suspension of magnesium turnings (44 g, 1.8 mole) in ether (225 mL) under nitrogen over a period of 1 hour. The mixture was stirred at room temperature for 1 hour, transferred into a 1000 mL addition funnel and then was added to a suspension of N-(phenylmethyl)-3,4-dimethylpyridinium chloride (350.7 g, 1.5 mole) in ether (1500 mL) under a nitrogen atmosphere. The reaction mixture was stirred at room temperature for 24 hours and was then poured into a solution of saturated ammonium chloride (3 L). The organic layer was separated and the aqueous layer was extracted with ether (1000 mL). The combined ether layers were washed with water (500 mL), then brine (500 mL) and were dried over sodium sulfate and potassium carbonate. The solvent was removed in vacuo to afford 284.1 g (76%) of 1,2-dihydro-N-(phenylmethyl)-2,3,4-trimethylpyridine as an amber oil.

Workup

  1. additiontransferred into a 1000 mL addition funnel
  2. stirringThe reaction mixture was stirred at room temperature for 24 hours
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with ether (1000 mL)
  5. washThe combined ether layers were washed with water (500 mL)
  6. dry with materialbrine (500 mL) and were dried over sodium sulfate and potassium carbonate
  7. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-27e39e3f0eb247b3a0b3b11c1ebaa605
Source dataset
uspto-grants-1994_03
Patent number
US05290796

Reaction notes

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