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

HRID 1471254

Reaction equation

HRID 1471254 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-6fcff27234cd4367af54cce2afaab700
Source dataset
uspto-grants-2015_04
Patent number
US09011734B2

Linked notes

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