Toluene → HCID 13652429, compound

HRID 615877Notes

Reaction equation

HRID 615877 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:9]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[CH3:10])=[CH:4][CH:3]=1.C1(C)C=CC=CC=1.[C:24](Cl)(=[O:30])[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]>C(N(CC)CC)C>[N:13]1[CH:14]=[CH:15][CH:16]=[C:11]([CH:9]([N:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[C:24](=[O:30])[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH3:10])[CH:12]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 67340Hexanoyl chlorideHCID 13652428HCID 13652428, compound

Product 1

HCID 13652429HCID 13652429, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a stirred solution of 7.5 g. of N-(4-chlorophenyl)-[1-(3-pyridyl)ethyl]amine in 200 ml. of toluene containing 5.0 g. of triethylamine were added dropwise over thirty minutes 4.5 g. of hexanoyl chloride. Following the complete addition, the solid precipitate which had formed was removed by filtration, and the solvent was removed from the filtrate by evaporation under reduced pressure. The product thus formed was chromatographed over a silica gel column to provide, after removal of the solvent from the appropriate factions, 650 mg. of N-[1-(3-pyridyl)ethyl]-N-(4-chlorophenyl)hexanamide. Oil.

Workup

  1. additionthe complete addition
  2. customthe solid precipitate which had formed
  3. customwas removed by filtration
  4. customthe solvent was removed from the filtrate by evaporation under reduced pressure
  5. customThe product thus formed
  6. customwas chromatographed over a silica gel column
  7. customto provide
  8. customafter removal of the solvent from the appropriate factions, 650 mg

Sources & evidence

ORD record
ord-aedccc5ba945484c82e66078c8d9fe7f
Source dataset
uspto-grants-1985_02
Patent number
US04501746

Reaction notes

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