1,2-Dichloroethane → HCID 20190421, compound

HRID 1788763Notes

Reaction equation

HRID 1788763 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:8]3[C:12](=[C:13]([C:15]([OH:17])=O)[CH:14]=2)[CH2:11][CH2:10][CH2:9]3)[CH:2]=1.CN(C)C=O.[Cl:23]CCCl>S(Cl)(Cl)=O.C1CCCCC1>[ClH:23].[Cl:23][C:15]([C:13]1[CH:14]=[C:7]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[N:8]2[C:12]=1[CH2:11][CH2:10][CH2:9]2)=[O:17]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 6228DimethylformamideHCID 21255155HCID 21255155, compound

Product 1

HCID 20190421HCID 20190421, compound

Reagents, catalysts & solvents 2

HCID 8078CyclohexaneSolventHCID 24386Thionyl ChlorideSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 5-(3-pyridyl)-2,3-dihydro-1H-pyrrolizine-7-carboxylic acid (11.4 g) in a mixture of thionyl chloride (17.4 cc), dimethylformamide (0.05 cc) and 1,2-dichloroethane (150 cc) is heated at a temperature of about 80° C. for 3 hours. The reaction mixture is cooled to a temperature of about 20° C. and concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature of about 60° C. The residue obtained is suspended in cyclohexane (250 cc) and the solvent is evaporated off under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature of about 60° C. The same operation is repeated twice. 7-Chloroformyl-5-(3-pyridyl)-2,3-dihydro-1H-pyrrolizine hydrochloride (14.1 g) is thus obtained in the form of yellow crystals melting at 230° C.

Workup

  1. temperatureThe reaction mixture is cooled to a temperature of about 20° C.
  2. concentrationconcentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature of about 60° C
  3. customThe residue obtained
  4. customthe solvent is evaporated off under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature of about 60° C

Sources & evidence

ORD record
ord-a0e2495416b24776b0ff2e14038ce5c9
Source dataset
uspto-grants-1987_08
Patent number
US04684658

Reaction notes

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