Methyl iodide → HCID 23371659, compound

HRID 1729200Notes

Reaction equation

HRID 1729200 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][CH2:11][CH:10]([CH3:14])[CH2:9]2)[N:5]=[C:4]([NH:15][CH3:16])[N:3]=1.[CH3:17][I:18]>O1CCOCC1>[I-:18].[CH3:17][N+:3]1[C:4]([NH:15][CH3:16])=[N:5][C:6]([N:8]2[CH2:13][CH2:12][CH2:11][CH:10]([CH3:14])[CH2:9]2)=[N:7][C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 23371661HCID 23371661, compound

Product 1

HCID 23371659HCID 23371659, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-methyl-6-methylamino-4-(3-methylpiperidino)-1,3,5-triazine (221 mg; 1 mM) and methyl iodide (0.5 ml; 8 mM) and dioxane (5 ml) was heated at reflux for 15 hours. The mixture was cooled, the solvent removed under reduced pressure and the residue was crystallised from a mixture of methanol and ether. There was thus obtained 1,2-dimethyl-6-methylamino-4-(3-methylpiperidino)-1,3,5-triazinium iodide (262 mg, 72% yield) m.p. 214°-214.5° C.; microanalysis found: C,39.7; H,5.8; N,19.3%; C12H22N5I requires: C,39.7; H,6.1; N,19.3%; NMR (200 MHz). (CDCl3): 0.95-1.05 (3H,q, piperidine 3--CH3), 1.2-2.0 (5H, complex, piperdine 3H, 4--CH2 and 5--CH2), 2.5-2.6 (3H, s, CH3), 2.6-3.15 (2H, complex, piperidine 2 --H axial and 6--H axial), 3.05-3.15 (3H,d, NHCH3), 3.9 (3H,s, N--CH3), 4.45-4.7 (2H, complex piperidine 2--H equatorial and 6--H equatorial), 8.6-8.8 (1H, br, NH). [Note: the site of quaternisation was confirmed by conventional nuclear Overhauser studies].

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 15 hours
  3. temperatureThe mixture was cooled
  4. customthe solvent removed under reduced pressure
  5. customthe residue was crystallised from a mixture of methanol and ether

Sources & evidence

ORD record
ord-be9fff8760ad4c4f8a0a78881e9365d5
Source dataset
uspto-grants-1994_07
Patent number
US05332737

Reaction notes

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