Sodium Hydroxide → Tris(2-pyridylmethyl)amine

HRID 1858881Notes

Reaction equation

HRID 1858881 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8]Cl.[OH-].[Na+].[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18][NH2:19]>O.ClCCl>[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][N:19]([CH2:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][N:2]=1)[CH2:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][N:12]=1

Participants

6

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 195092-PyridinemethanamineHCID 23392Picolyl chloride hydrochloride

Product 1

HCID 379259Tris(2-pyridylmethyl)amineYield 54.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

5.0 g (30.5 mmoles) of 2-picolyl chloride hydrochloride were dissolved in 13 ml of water and 6 ml of 5.3 N NaOH were added to the resulting solution while cooling with ice. The red suspension obtained was cooled to 0° C. and a solution of 1.64 g (15.25 mmoles) of picolylamine in 26 ml of dichloromethane was added. The mixture was heated to room temperature and reacted with another 6 ml of 5.3 N NaOH over a period of several days during which measures were taken to ensure that the pH value did not rise above 9.5. The mixture was then washed twice with 7 ml of 15% NaOH and the organic phase was dried over sodium sulfate. After the drying agent had been removed, the solvent was evaporated off. The brown residue was extracted with ether and the solid obtained was recrystallized from ether. 2.4 g of tris-(2-pyridylmethyl)-amine were obtained.

Workup

  1. temperaturewhile cooling with ice
  2. customThe red suspension obtained
  3. temperatureThe mixture was heated to room temperature
  4. washThe mixture was then washed twice with 7 ml of 15% NaOH
  5. dry with materialthe organic phase was dried over sodium sulfate
  6. customAfter the drying agent had been removed
  7. customthe solvent was evaporated off
  8. extractionThe brown residue was extracted with ether
  9. customthe solid obtained
  10. customwas recrystallized from ether

Sources & evidence

ORD record
ord-4410a7e1991f445bab62e37f9b056168
Source dataset
uspto-grants-2000_11
Patent number
US06153576

Reaction notes

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