2-Chloropyridine → HCID 15858758, compound

HRID 580853Notes

Reaction equation

HRID 580853 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>[OH:11][CH2:10][C@@H:9]1[CH2:12][CH2:13][CH2:14][N:8]1[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1

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-91f9e540f16b4f02b41bb4ebd62af0bf
Source dataset
uspto-grants-1999_07
Patent number
US05919782

Reaction notes

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