2-Chloropyridine → HCID 15858758, compound

HRID 2392545Notes

Reaction equation

HRID 2392545 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[NH:8]1[CH2:14][CH2:13][CH2:12][C@H:9]1[CH2:10][OH:11]>O>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[N:8]1[CH2:14][CH2:13][CH2:12][C@H:9]1[CH2:10][OH:11]

Participants

4

Reactant 2

HCID 79772-ChloropyridineHCID 640091L-Prolinol

Product 1

HCID 15858758HCID 15858758, compoundYield 54.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 2-chloropyridine (118 g) and L-prolinol (70 g) was heated under nitrogen atmosphere at 160° C. with stirring for 4 h. The mixture was cooled to room temperature and poured into water and the solution was extracted with chloroform repeatedly. The combined organic extracts were dried (Na2SO4) and concentrated. The crude product was purified by column chromatography using 2% MeOH in CHCl3 as eluent to get 67.3 g (54.5%) of the title compound as a syrupy liquid.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionthe solution was extracted with chloroform repeatedly
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. concentrationconcentrated
  5. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-41464de8fb2744cca22a68ab6bedc7b8
Source dataset
uspto-grants-1998_09
Patent number
US05801173

Reaction notes

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