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

HRID 2294071Notes

Reaction equation

HRID 2294071 reaction equation
[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[CH:6]([C:16]3[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH:17]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[I:23]C.[CH3:25]COCC>CO>[I-:23].[CH:12]1[C:8]2[CH2:9][CH2:10][C:11]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=3[CH:6]([C:16]3[CH2:21][CH2:20][N+:19]([CH3:25])([CH3:22])[CH2:18][CH:17]=3)[C:7]=2[CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6328Methyl iodideHCID 214741334-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)-1-methyl-1,2,5,6-tetrahydropyridine

Product 1

HCID 214741354-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)-1,1-dimethyl-1,2,5,6-tetrahydropyridinium iodideYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dissolved 4-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)-1-methyl-1,2,5,6-tetrahydropyridine (0.80 g, 2.8 mmol) in 25 mL of methanol, and added 1 mL of iodomethane. Refluxed for 1 hour. Cooled to room temperature, and evaporated. Triturated solid with 1:2 acetonitrile:ether to give 1.1 g (92% yield) of 4-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)-1,1-dimethyl-1,2,5,6-tetrahydropyridinium iodide as a cream solid.

Workup

  1. temperatureRefluxed for 1 hour
  2. customevaporated
  3. customTriturated solid with 1:2 acetonitrile

Sources & evidence

ORD record
ord-42d134a72c3444899671148315fa3f48
Source dataset
uspto-grants-1997_11
Patent number
US05688805

Reaction notes

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