Pyridine → HCID 86734063, compound

HRID 1287547Notes

Reaction equation

HRID 1287547 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:7](Cl)(=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C[N:17]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)C1C=CC=CC=1>[Cu].C1(C)C=CC=CC=1>[CH3:7][C:8]1[CH:13]=[CH:12][C:11]([C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)=[C:10]([NH:17][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:9]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 69191N-Methyl-N-phenylbenzylamine

Product 1

HCID 86734063HCID 86734063, compound

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 1140TolueneSolvent

Procedure

158 parts of pyridine and 155 parts of benzoyl chloride are heated with 4 parts of copper powder for an hour at 100° to 105° C. At 70° to 80° C there is then added 197 parts of methylbenzylaniline and heating is continued for another five hours at 100° to 105° C. When the reaction is over 800 parts of toluene is added at 70° to 80° C, and the precipitate is suction filtered and dissolved in 1,000 parts of 5% hydrochloric acid. The product is clarified with animal charcoal and reprecipitated in the cold with ammonia and recrystalized from a mixture of ethanol and water for further purification. 50 parts of 4-(4'-methylbenzylaminophenyl)-pyridine is obtained as practically colorless crystals which melt at 118° to 119° C.

Workup

  1. temperatureheating
  2. additionis added at 70° to 80° C
  3. filtrationfiltered
  4. dissolutiondissolved in 1,000 parts of 5% hydrochloric acid
  5. customreprecipitated in the cold with ammonia
  6. customrecrystalized from a mixture of ethanol and water for further purification

Sources & evidence

ORD record
ord-a41a0a74bbdc4452ba106ca6e0ff8341
Source dataset
uspto-grants-1976_10
Patent number
US03985376

Reaction notes

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