Methyl iodide → HCID 19710005, compound

HRID 725895Notes

Reaction equation

HRID 725895 reaction equation
[CH3:1][O:2][C:3]1[C:11]2[O:10][C:9]([C:12]3[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=3)=[CH:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.[CH3:18][I:19]>CC(=O)CC>[I-:19].[CH3:18][N+:15]1[CH:16]=[CH:17][C:12]([C:9]2[O:10][C:11]3[C:3]([O:2][CH3:1])=[CH:4][CH:5]=[CH:6][C:7]=3[CH:8]=2)=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 22733883HCID 22733883, compound

Product 1

HCID 19710005HCID 19710005, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 4-(7-methoxy-2-benzofuranyl)pyridine (66 g), methyl iodide (56.7 g) and 2-butanone (800 ml) was stirred at 50° C. for 4 hours, cooled to room temperature, filtered and the resulting solid was washed with 2-butanone to provide 1-methyl-4-(7-methoxy-2-benzofuranyl)pyridinium iodide, m.p. 225°-227° (dec.). The quaternary salt (90 g) was dissolved in methanol (1 l) and a solution of NaBH4 (40 g) in H2O (250 ml) was added dropwise. The mixture was stirred at ambient temperature for 3 hours, concentrated and the residual aqueous layer was extracted with DCM. The extracts were combined, washed with brine and concentrated to give 1-methyl-4-(7-methoxy-2-benzofuranyl)-1,2,3,6-tetrahydropyridine.

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. washthe resulting solid was washed with 2-butanone

Sources & evidence

ORD record
ord-dee5f336eb624ea5ab7fc17d0a50c382
Source dataset
uspto-grants-1998_01
Patent number
US05708007

Reaction notes

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