Benzaldehyde → 2-Cyclohexyl-1-(pyridin-2-YL)ethanamine

HRID 52571Notes

Reaction equation

HRID 52571 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][NH2:8].[CH:9](=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[OH-].[K+].C1(CBr)CCCCC1.Cl>C1(C)C=CC=CC=1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]([NH2:8])[CH2:9][CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

8

Reactant 5

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 195092-PyridinemethanamineHCID 137636Cyclohexane, (bromomethyl)-

Product 1

HCID 97942552-Cyclohexyl-1-(pyridin-2-YL)ethanamineYield 45%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 2.16 g of 2-picolylamine (20 mmoles) and 2.12 g of benzaldehyde (20 mmoles) was stirred for 5-20 hours. The reaction mixture was diluted with 20 ml of toluene with stirring, then 1.12 g (20 mmoles) of potassium hydroxide added followed by the addition of 3.7 g of tetrabutylammonium iodide (10 mmoles) and 3.55 g of cyclohexylmethyl bromide (20 mmoles). The mixture was refluxed for 6-24 hours, then cooled and stirred with 10 ml of a 2N HCl for 2-6 hours. The organic phase was discarded, the aqueous acidic phase was washed with methylene chloride. The aqueous phase was basified with ammonium hydroxide and the racemic amine extracted with methylene chloride to yield 45%-55% racemic 1-(2-pyridyl)-2-cyclohexylethylamine as a light yellow oil.

Workup

  1. stirringwith stirring
  2. temperatureThe mixture was refluxed for 6-24 hours
  3. temperaturecooled
  4. washthe aqueous acidic phase was washed with methylene chloride
  5. extractionthe racemic amine extracted with methylene chloride

Sources & evidence

ORD record
ord-bf5b6c8777854172b971743bd4be160b
Source dataset
uspto-grants-1997_04
Patent number
US05616717

Reaction notes

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