Methyl iodide → 4-[(Ethylthio)methyl]-1-methyl-1,2,3,6-tetrahydropyridine

HRID 21371Notes

Reaction equation

HRID 21371 reaction equation
[CH2:1]([S:3][CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[CH:7][CH:6]=1)[CH3:2].[CH3:11]I>C(#N)C>[CH2:1]([S:3][CH2:4][C:5]1[CH2:6][CH2:7][N:8]([CH3:11])[CH2:9][CH:10]=1)[CH3:2]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 144422054-[(Ethylthio)methyl]pyridine

Product 1

HCID 144422154-[(Ethylthio)methyl]-1-methyl-1,2,3,6-tetrahydropyridineYield 47.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

8.2 g (0.054 mol) of 4-[(ethylthio)methyl]pyridine are dissolved in 60 ml of acetonitrile and then 9.1 g of methyliodide are added. After 12 hours the reaction mixture is evaporated down in vacuo. The residue is reacted analogously to Example 1 b) with sodium borohydride in methanol and worked up. The crude product obtained is distilled (5.2 g; 56.3% of theory; b.p. 118°-120° C./20 mbar) and then chromatographed on neutral aluminium oxide using chloroform as eluant. 4.4 g of 4-[(ethylthio)methyl]-1-methyl-1,2,3,6-tetrahydropyridine are obtained, which is converted with one equivalent of maleic acid into the maleate (m.p. 102°-105° C., from ethyl acetate).

Workup

  1. customAfter 12 hours the reaction mixture is evaporated down in vacuo
  2. customThe residue is reacted analogously to Example 1 b) with sodium borohydride in methanol
  3. customThe crude product obtained
  4. distillationis distilled (5.2 g; 56.3% of theory; b.p. 118°-120° C./20 mbar)
  5. customchromatographed on neutral aluminium oxide

Sources & evidence

ORD record
ord-833ce92ccfa44f91b77719638dad4bee
Source dataset
uspto-grants-1995_06
Patent number
US05422353

Reaction notes

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