Hydrochloric Acid → HCID 131730754, compound

HRID 80868Notes

Reaction equation

HRID 80868 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)=[CH:4][N:3]=1.CS(C)=O.[CH:20]([N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)([CH3:22])[CH3:21].[ClH:29]>O>[ClH:1].[ClH:29].[CH3:15][O:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]2[CH:6]=[CH:7][C:2]([N:26]3[CH2:27][CH2:28][N:23]([CH:20]([CH3:22])[CH3:21])[CH2:24][CH2:25]3)=[N:3][CH:4]=2)=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 780131-IsopropylpiperazineHCID 121945632-Chloro-5-(4-methoxyphenyl)pyridine

Product 1

HCID 131730754HCID 131730754, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 2-chloro-5-(4-methoxyphenyl)pyridine (200 mg, 0.91 mmol), dry DMSO (2.0 mL) and 1-isopropylpiperazine (500 mg, 3.9 mmol) was stirred and heated on a 130° C. oil-bath overnight, then at 150° C. for 4 h, left 2 days at rt and finally heated at 140° C. overnight. The reaction mixture was allowed to cool and then poured into water (100 mL). The mixture was extracted with ethyl acetate (100 mL), and the organic extract was washed with water and dried (MgSO4). The solvent was evaporated to give a solid residue which was dissolved into 0.5 N hydrochloric acid (20 mL). A small insoluble solid was removed by filtration, and the aqueous solution was evaporated to give a residue which was re-evaporated with absolute ethanol. The resulting solid was re-crystallised from absolute ethanol to give 210 mg (60%) of 1-[5-(4-methoxyphenyl)pyridin-2-yl]-4-isopropylpiperazine, dihydrochloride.

Workup

  1. waitleft 2 days at rt
  2. temperaturefinally heated at 140° C. overnight
  3. temperatureto cool
  4. extractionThe mixture was extracted with ethyl acetate (100 mL)
  5. extractionthe organic extract
  6. washwas washed with water
  7. dry with materialdried (MgSO4)
  8. customThe solvent was evaporated
  9. customto give a solid residue which
  10. customA small insoluble solid was removed by filtration
  11. customthe aqueous solution was evaporated
  12. customto give a residue which
  13. customwas re-evaporated with absolute ethanol
  14. customThe resulting solid was re-crystallised from absolute ethanol

Sources & evidence

ORD record
ord-8401e3ca4bee44d9a9c774d8e0b1c61f
Source dataset
uspto-grants-2014_09
Patent number
US08846677B2

Reaction notes

Loading…