Potassium Hydroxide → N,N-Bis(pyridin-2-ylmethyl)propan-1-amine

HRID 495252

Reaction equation

HRID 495252 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.[OH-].[K+].I[CH2:19][CH2:20][CH3:21]>CN(C)C=O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][N:8]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)[CH2:19][CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 336431-IodopropaneHCID 73759Bis(2-pyridylmethyl)amine

Product 1

HCID 59816448N,N-Bis(pyridin-2-ylmethyl)propan-1-amineYield 53.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a flask were added 1.0 g di-(2-picolyl)amine, 0.85 g of pulverized potassium hydroxide and 15 ml of N,N-dimethylformamide. After stirring for 1 hour under nitrogen, the mixture was cooled to 5 C and 1.7 g of 1-iodopropane were added. The mixture was heated to 35 C and stirred for 16 hours. After quenching with 30 ml water, the product was extracted with ethyl acetate and washed twice with water. Following removal of solvent, the product was purified by silica gel chromatography using ethyl acetate to give 0.65 g of a yellow oil.

Workup

  1. additionwere added
  2. temperatureThe mixture was heated to 35 C
  3. stirringstirred for 16 hours
  4. customAfter quenching with 30 ml water
  5. extractionthe product was extracted with ethyl acetate
  6. washwashed twice with water
  7. customremoval of solvent
  8. customthe product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-8dff10f15cfe4ff69c9854119eb0a28e
Source dataset
uspto-grants-2009_05
Patent number
US07538931B2

Linked notes

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