Methyl iodide → 2-Methyl-2-phenyl-1,2,3,4-tetrahydroisoquinolin-2-ium iodide

HRID 2292109Notes

Reaction equation

HRID 2292109 reaction equation
[C:1]1([N:7]2[CH2:16][CH2:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:17][I:18]>CC(C)=O>[I-:18].[CH3:17][N+:7]1([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:16][CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8]1

Participants

4

Reactant 2

HCID 6328Methyl iodide2×HCID 11321753HCID 11321753, compound

Product 1

HCID 132116242-Methyl-2-phenyl-1,2,3,4-tetrahydroisoquinolin-2-ium iodide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-phenyl-1,2,3,4-tetrahydroisoquinoline (1.01 g,) was dissolved in acetone (10 ml) and methyl iodide (0.794 g,) was added. The clear solution stood at -20° for 48 hr when t.l.c. indicated the presence of unchanged starting material. A further quantity of methyl iodide (0.3 ml) was added and the reaction mixture was heated at reflux for 3 hrs. The solvent was removed in vacuo and the residue triturated with ether. The resulting solid 1,2,3,4-tetrahydro-2-methyl-2-phenylisoquinolinium iodide was filtered off and dried (1 g). m.pt. softens 190°, melts 195° (decomp.)

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 3 hrs
  3. customThe solvent was removed in vacuo
  4. customthe residue triturated with ether
  5. filtrationThe resulting solid 1,2,3,4-tetrahydro-2-methyl-2-phenylisoquinolinium iodide was filtered off
  6. customdried (1 g)
  7. customsoftens 190°

Sources & evidence

ORD record
ord-fbc1ab5cdddd45488f7e2575eca11cc6
Source dataset
uspto-grants-1989_01
Patent number
US04801593

Reaction notes

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