Potassium Carbonate → HCID 22995379, compound

HRID 1167065Notes

Reaction equation

HRID 1167065 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7](Cl)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1.[N:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH2:21][NH:22][CH2:23][CH2:24][CH2:25][NH:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[N:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH2:21][N:22]([CH2:23][CH2:24][CH2:25][N:26]([CH2:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)[CH:27]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:8][N:9]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1)[CH:7]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 300760N,N'-bis(pyrid-2-ylmethyl)-1,3-diamino-propaneHCID 14575144117106-10-2

Product 1

HCID 22995379HCID 22995379, compoundYield 64.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1.7 g dipyridyl-methylchloride (14), 1 g N,N′-bis(pyrid-2-ylmethyl)-1,3-diamino-propane (15) and 0.5 g potassium carbonate in 20 ml acetonitrile was stirred and refluxed under argon for 48 h. TLC (silica/eluent CH2Cl2/MeOH(7N NH3) 90/10) indicated the reaction to be almost complete. The mixture was filtered and evaporated. The residue was chromatographed on silica using dichloromethane with increasing methanol concentration (up to 5%) to give 1.5 g pure product as a yellow/brown glassy gum.

Workup

  1. temperaturerefluxed under argon for 48 h
  2. customthe reaction
  3. filtrationThe mixture was filtered
  4. customevaporated
  5. customThe residue was chromatographed on silica
  6. concentrationwith increasing methanol concentration (up to 5%)

Sources & evidence

ORD record
ord-f6656fd3537741518b261ffa4ad28812
Source dataset
uspto-grants-2003_09
Patent number
US06617299B1

Reaction notes

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