Pyridine → HCID 14097263, compound

HRID 568363Notes

Reaction equation

HRID 568363 reaction equation
[C:1]1([CH:7]([OH:16])[C:8]#[C:9][CH2:10][N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.Cl.C(Cl)C1C=CC=NC=1.[O:32]1CCC[CH2:33]1>>[C:33]([O:16][CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:8]#[C:9][CH2:10][N:11]([CH2:12][CH3:13])[CH2:14][CH3:15])(=[O:32])[C:19]1[CH:20]=[CH:21][CH:22]=[N:17][CH:18]=1

Participants

5

Reactant 4

HCID 1049PyridineHCID 8028TetrahydrofuranHCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 2840585HCID 2840585, compound

Product 1

HCID 14097263HCID 14097263, compoundYield 46.6%

Procedure

Dissolved in anhydrous tetrahydrofuran was 2.17 g of N-(4-phenyl-4-hydroxy-2-butynyl)-N,N-diethylamine, followed by an addition of 4 ml of pyridine. Then, 1.78 g of nicotinyl chloride hydrochloride was added at room temperature little by little. The resultant mixture was thereafter reacted at the same temperature for 4 hours. After the reaction, the solvent was distilled off under reduced pressure and the residue was taken up in chloroform. The resultant chloroform solution was washed with water and was then dried over anhydrous sodium sulfate. The chloroform was distilled off under reduced pressure and the residue was purified by column chromatography (silica gel) to obtain 1.5 g of the intended product as a light yellowish oily substance (yield: 46.6%).

Workup

  1. customAfter the reaction
  2. distillationthe solvent was distilled off under reduced pressure
  3. washThe resultant chloroform solution was washed with water
  4. dry with materialwas then dried over anhydrous sodium sulfate
  5. distillationThe chloroform was distilled off under reduced pressure
  6. customthe residue was purified by column chromatography (silica gel)

Sources & evidence

ORD record
ord-2eb7ca2162fc4073adfa80efb78f58b4
Source dataset
uspto-grants-1988_03
Patent number
US04728659

Reaction notes

Loading…