Thionyl Chloride → HCID 131722401, compound

HRID 636573Notes

Reaction equation

HRID 636573 reaction equation
S(Cl)(Cl)=O.N1C=CC=C([C:11]2[N:19]3[C:14]([CH2:15][CH2:16][CH2:17][CH2:18]3)=[C:13]([C:20]([OH:22])=[O:21])[CH:12]=2)C=1>C(Cl)(Cl)Cl.CN(C)C=O>[N:19]1[CH:14]=[CH:15][CH:16]=[C:17]([C:12]2[C:13]([C:20]([OH:22])=[O:21])=[C:14]3[N:19]([CH:11]=2)[CH2:18][CH2:17][CH2:16][CH2:15]3)[CH:18]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 21255107HCID 21255107, compound

Product 1

HCID 131722401HCID 131722401, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6212ChloroformSolvent

Procedure

4.3 cm3 of thionyl chloride are added dropwise to a suspension 4.8 g of 3-(3-pyridyl)-5,6,7,8-tetrahydroindolizine-1-carboxylic acid in 120 cm3 of chloroform, followed by a few drops of dimethylformamide. The resulting suspension is then stirred at ambient temperature for 16 hours (slow gas release) and is then heated to reflux (75° C.) for 1 hour, at the end of which there is no further gas release. It is then cooled to ambient temperature and then concentrated at reduced pressure (2.7 kPa) and taken up twice in ethanol-free dichloromethane and then concentrated again in the same way. 5.4 g of 3-(3-pyridyl-5,6,7,8-tetrahydroindolizine-1-carboxylic acid are thus obtained in the form of a greenish solid. (Rf=0.44; thin layer chromatography on silica gel; eluent: 10/90 by volume mixture of methanol and of dichloromethane).

Workup

  1. temperatureis then heated
  2. temperatureto reflux (75° C.) for 1 hour
  3. temperatureIt is then cooled to ambient temperature
  4. concentrationconcentrated at reduced pressure (2.7 kPa)
  5. concentrationconcentrated again in the same way

Sources & evidence

ORD record
ord-1038226b792845a0a219ed36c1a4c3c8
Source dataset
uspto-grants-2001_02
Patent number
US06194426B1

Reaction notes

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