Diethyl Ether → 1-Hexyl-4-methylpyridin-1-ium bromide

HRID 644794Notes

Reaction equation

HRID 644794 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH3:7])=[CH:3][CH:2]=1.[Br:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].C(#N)C.CCOCC>C(Cl)(Cl)Cl>[Br-:8].[CH2:9]([N+:1]1[CH:6]=[CH:5][C:4]([CH3:7])=[CH:3][CH:2]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6342AcetonitrileHCID 79634-MethylpyridineHCID 81011-Bromohexane

Product 1

HCID 670559921-Hexyl-4-methylpyridin-1-ium bromideYield 92%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 4.65 g of 4-picoline (50 mmol), 9.90 g of 1-bromohexane (60 mmol) and 30 mL of acetonitrile was refluxed for three hours and then cooled to room temperature. The viscous mixture was then added dropwise into 100 mL of ether with vigorous stirring. The mixture was let to stand for a while and then the upper ether layer was decanted. The residual viscous solution was dissolved in 10 mL of acetonitrile again and dispersed into 100 mL of ether. This procedure was repeated two more times in order to completely remove the unreacted starting materials. The resulting viscous liquid was dried under vacuum to give 11.8 g of off-white wax (92% yield). 1H NMR (DMSO-d6, 400 MHz): 0.89 (t, 3H), 1.26 (m, 4H), 1.85 (m, 4H), 2.64 (s, 3H), 4.81 (t, 2H), 8.0 (m, 2H), 8.9 (m, 2H); IR (CHCl3, cm−1): 1398 (C═C), 1635 (C═N), 2975 (N—C).

Workup

  1. customthe upper ether layer was decanted
  2. dissolutionThe residual viscous solution was dissolved in 10 mL of acetonitrile again
  3. additiondispersed into 100 mL of ether
  4. customto completely remove the
  5. customThe resulting viscous liquid was dried under vacuum
  6. customto give 11.8 g of off-white wax (92% yield)

Sources & evidence

ORD record
ord-0ff398bea20240fcb35169e3075b3260
Source dataset
uspto-grants-2010_04
Patent number
US07700780B2

Reaction notes

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