Methanol → HCID 86734108, compound

HRID 1288521Notes

Reaction equation

HRID 1288521 reaction equation
[CH3:1][CH:2]([N:14]([CH3:16])[CH3:15])[CH2:3][CH2:4][CH:5]1[C:10]([CH3:12])([CH3:11])[CH2:9][CH2:8][CH2:7][CH:6]1[CH3:13].[CH2:17](Br)[C:18]#C.[I-:21].[K+].[CH3:23]O>O>[I-:21].[CH3:1][CH:2]([N+:14]([CH3:23])([CH3:15])[CH2:16][C:17]#[CH:18])[CH2:3][CH2:4][CH:5]1[C:10]([CH3:11])([CH3:12])[CH2:9][CH2:8][CH2:7][CH:6]1[CH3:13]

Participants

6

Reactant 4

HCID 887MethanolHCID 4875Potassium IodideHCID 7842Propargyl bromideHCID 21502500HCID 21502500, compound

Product 1

HCID 86734108HCID 86734108, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of [1-methyl-3-(2,6,6-trimethylcyclohexyl)propyl]dimethylamine (3.0 g) and propargylbromide (3.0 g) in methanol (20 cc) was refluxed for 1 hour, and thereto was added a solution of potassium iodide (4.5 g) in water (15 cc). After shaking the mixture, water (50 cc) was added thereto, and the aqueous solution was extracted with chloroform, The chloroform layer was washed with water, dried and concentrated to dryness. The residue was recrystallized from a mixed solvent of ethanol and ether to give colorless crystals (4.5 g) of [1-methyl-3-(2,6,6-trimethylcyclohexyl)propyl]dimethylpropargylammonium iodide, m.p. 165°-167° C.

Workup

  1. additionwas added
  2. extractionthe aqueous solution was extracted with chloroform
  3. washThe chloroform layer was washed with water
  4. customdried
  5. concentrationconcentrated to dryness
  6. customThe residue was recrystallized from a mixed solvent of ethanol and ether

Sources & evidence

ORD record
ord-83d8ae8da0744796945effa674924ee2
Source dataset
uspto-grants-1976_10
Patent number
US03988373

Reaction notes

Loading…