Trimethylamine → HCID 129667418, compound

HRID 1706156Notes

Reaction equation

HRID 1706156 reaction equation
CN([C:4]1[C-:5]([CH3:9])[CH:6]=[CH:7][CH:8]=1)C.[CH-:10]1[CH:14]=[CH:13][CH:12]=[CH:11]1.[Fe+2:15].[C-]#N.[K+].[CH3:19][N:20](C)C>O>[C:19]([CH2:9][C-:5]1[CH:4]=[CH:8][CH:7]=[CH:6]1)#[N:20].[CH-:10]1[CH:14]=[CH:13][CH:12]=[CH:11]1.[Fe+2:15]

Participants

5

Reactant 3

HCID 1146TrimethylamineHCID 9032Potassium CyanideHCID 129690005HCID 129690005, compound

Product 1

HCID 129667418HCID 129667418, compoundYield 76.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

58 g (0.15 mol) of N,N-dimethylamino-methylferrocene methoiodide were added to a solution of 57 g (0.88 mol) of potassium cyanide in 570 ml of water and the mixture was heated to the boil, the solid material dissolving. Within a few minutes, the evolution of trimethylamine started, while at the same time a volatile oil separated out. After stirring for two hours under reflux, the mixture was cooled to room temperature, whereupon the oily product solidified. The solid material was separated off and the solution which remained was extracted with ether. The combined organic phases were washed with water and, after drying over sodium sulphate, were concentrated under reduced pressure. The residue was recrystallized from 200 ml of hexane. 26 g (76.9% of theory) of cyanomethylferrocene of melting point 82° to 83° C. were obtained in this manner.

Workup

  1. temperaturethe mixture was heated to the boil
  2. dissolutionthe solid material dissolving
  3. waitWithin a few minutes
  4. customseparated out
  5. temperatureunder reflux
  6. customThe solid material was separated off
  7. extractionthe solution which remained was extracted with ether
  8. washThe combined organic phases were washed with water
  9. dry with materialafter drying over sodium sulphate
  10. concentrationwere concentrated under reduced pressure
  11. customThe residue was recrystallized from 200 ml of hexane

Sources & evidence

ORD record
ord-d0b132c004094876871131f2031c057a
Source dataset
uspto-grants-1980_06
Patent number
US04206227

Reaction notes

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