4,4'-Bipyridine → HCID 21959970, compound

HRID 2214232Notes

Reaction equation

HRID 2214232 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][Br:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)=[CH:13][CH:12]=1>C1(C)C=CC=CC=1>[Br-:10].[N:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][N+:20]([CH2:9][CH2:8][CH2:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:19][CH:18]=2)=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 111074,4'-BipyridineHCID 12503(3-Bromopropyl)benzene

Product 1

HCID 21959970HCID 21959970, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

9.6 g of 3-phenyl-1-bromopropane were added dropwise over the course of 45 min to 15.0 g of 4,4′-bipyridyl in 90 ml of toluene at 70° C. The mixture was stirred for 24 h at reflux temperature, cooled down and the solid was filtered off with suction. The solid was stirred in 90 ml of toluene for 4 h at reflux temperature, cooled down, filtered off with suction and washed with toluene. Drying in vacuo gave 14.3 g (85% of theory) 4-(4-pyridyl)-1-(3-phenylpropyl)pyridinium bromide.

Workup

  1. temperatureat reflux temperature
  2. temperaturecooled down
  3. filtrationthe solid was filtered off with suction
  4. stirringThe solid was stirred in 90 ml of toluene for 4 h
  5. temperatureat reflux temperature
  6. temperaturecooled down
  7. filtrationfiltered off with suction
  8. washwashed with toluene
  9. customDrying in vacuo

Sources & evidence

ORD record
ord-11fef20ded364edf8cb337baaab9f248
Source dataset
uspto-grants-2006_09
Patent number
US07106489B2

Reaction notes

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