Methyl iodide → 4-[10,11-dihydro-5-(2-propenyl)-5H-dibenzo[a,d]cyclohepten-5-yl]-1,1-dimethyl-1,2,5,6-tetrahydropyridinium iodide

HRID 2294065

Reaction equation

HRID 2294065 reaction equation
[CH2:1]([C:4]1([C:19]2[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH:20]=2)[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][CH2:7][C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]1=2)[CH:2]=[CH2:3].[I:26][CH3:27]>C(O)C>[I-:26].[CH2:1]([C:4]1([C:19]2[CH2:24][CH2:23][N+:22]([CH3:27])([CH3:25])[CH2:21][CH:20]=2)[C:5]2[CH:18]=[CH:17][CH:16]=[CH:15][C:6]=2[CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]1=2)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 97975634-[10,11-dihydro-5-(2-propenyl)-5H-dibenzo[a,d]cyclohepten-5-yl]-1-methyl-1,2,5,6-tetrahydropyridine

Product 1

HCID 214741394-[10,11-dihydro-5-(2-propenyl)-5H-dibenzo[a,d]cyclohepten-5-yl]-1,1-dimethyl-1,2,5,6-tetrahydropyridinium iodideYield 66%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Dissolved 4-[10,11-dihydro-5-(2-propenyl)-5H-dibenzo[a,d]cyclohepten-5-yl]-1-methyl-1,2,5,6-tetrahydropyridine (0.50 g, 1.5 mmol) in 30 mL of absolute ethanol, and added 1 mL of iodomethane. Refluxed for 1 hour. Cooled to room temperature, and evaporated to a solid. Triturated with ether, and then recrystallized from dichloromethane-ether to give 0.47 g (66% yield) of 4-[10,11-dihydro-5-(2-propenyl)-5H-dibenzo[a,d]cyclohepten-5-yl]-1,1-dimethyl-1,2,5,6-tetrahydropyridinium iodide as a yellow solid.

Workup

  1. temperatureRefluxed for 1 hour
  2. customevaporated to a solid
  3. customTriturated with ether
  4. customrecrystallized from dichloromethane-ether

Sources & evidence

ORD record
ord-438bbb1f5ca0412a99e48911655b87eb
Source dataset
uspto-grants-1997_11
Patent number
US05688805

Linked notes

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