N-bromobutanimide → HCID 21255187, compound

HRID 636553Notes

Reaction equation

HRID 636553 reaction equation
[Br:1]N1C(=O)CCC1=O.Cl[C:10]1[C:15]([C:16]2[N:24]3[C:19]([CH2:20][CH2:21][CH2:22][CH2:23]3)=[C:18]([C:25]#[N:26])[CH:17]=2)=[CH:14][CH:13]=[CH:12][N:11]=1>ClCCCl>[Br:1][C:17]1[C:18]([C:25]#[N:26])=[C:19]2[N:24]([C:16]=1[C:15]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1)[CH2:23][CH2:22][CH2:21][CH2:20]2

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 21255174HCID 21255174, compound

Product 1

HCID 21255187HCID 21255187, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

2.42 g of N-bromosuccinimide are added with stirring to a solution of 3.5 g of 3-(2-chloro-3-pyridyl)-5,6,7,8-tetrahydroindolizine-1-carbonitrile in 50 cm3 of 1,2-dichloroethane. The mixture is refluxed for 20 hours. After cooling, the reaction mixture is concentrated at reduced pressure (2.7 kPa) at a temperature close to 60° C. The residue is taken up with 100 cm3 of ethyl acetate and washed 3 times with 70 cm3 of an aqueous solution of sodium bicarbonate at a concentration of 5%. The organic extracts are combined and dried over anhydrous magnesium sulphate, filtered and concentrated to dryness at reduced pressure (2.7 kPa) at a temperature close to 50° C. A mixture of products is thus obtained, which is chromatographed on a column of 1.8 cm diameter containing 90 g of silica (0.04-0.0063). Elution is carried out with dichloromethane at a total pressure of 1.5 bar and with 20-cm3 fractions being collected. The homogeneous fractions are combined and concentrated at reduced pressure (2.7 kPa) at a temperature close to 60° C. 2.79 g of 2-bromo-3-(3-pyridyl)-5,6,7,8-tetrahydroindolizine-1-carbonitrile are thus obtained in the form of white crystals melting at 188° C.

Workup

  1. temperatureThe mixture is refluxed for 20 hours
  2. temperatureAfter cooling
  3. concentrationthe reaction mixture is concentrated at reduced pressure (2.7 kPa) at a temperature
  4. customclose to 60° C
  5. washwashed 3 times with 70 cm3 of an aqueous solution of sodium bicarbonate at a concentration of 5%
  6. dry with materialdried over anhydrous magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness at reduced pressure (2.7 kPa) at a temperature
  9. customclose to 50° C
  10. additionA mixture of products
  11. customis thus obtained
  12. customwhich is chromatographed on a column of 1.8 cm diameter
  13. additioncontaining 90 g of silica (0.04-0.0063)
  14. washElution
  15. custombeing collected
  16. concentrationconcentrated at reduced pressure (2.7 kPa) at a temperature
  17. customclose to 60° C

Sources & evidence

ORD record
ord-63ecab8d32f648b193380da92ae37cab
Source dataset
uspto-grants-2001_02
Patent number
US06194426B1

Reaction notes

Loading…