Methanol → 3-Chloro-4-[4-[(6-chloroimidazo[1,2-a]pyridin-2-yl)methyl]-1-piperazinyl]benzamide

HRID 1416271Notes

Reaction equation

HRID 1416271 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N:10]1[CH2:15][CH2:14][N:13]([CH2:16][C:17]2[N:18]=[C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][N:20]3[CH:26]=2)[CH2:12][CH2:11]1)[C:5]#[N:6].[OH-].[Na+].C([OH:33])(C)(C)C.CO>OO.ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N:10]1[CH2:15][CH2:14][N:13]([CH2:16][C:17]2[N:18]=[C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][N:20]3[CH:26]=2)[CH2:12][CH2:11]1)[C:5]([NH2:6])=[O:33]

Participants

7

Reactant 4

HCID 887MethanolHCID 6386tert-ButanolHCID 14798Sodium HydroxideHCID 193671143-Chloro-4-[4-[(6-chloroimidazo[1,2-a]pyridin-2-yl)methyl]-1-piperazinyl]benzonitrile

Product 1

HCID 193671433-Chloro-4-[4-[(6-chloroimidazo[1,2-a]pyridin-2-yl)methyl]-1-piperazinyl]benzamide

Reagents, catalysts & solvents 2

HCID 784Hydrogen PeroxideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-chloro-4-[4-[(6-chloroimidazo[1,2-a]pyridin-2-yl)methyl]-1-piperazinyl]benzonitrile (Example 29; 0.122 g), NaOH (0.063 g), 30% hydrogen peroxide (2 drops), and tert-butanol (2 mL) is stirred at 80° C. for 4 h, after which it is cooled and concentrated under reduced pressure. The residue is partitioned between dichloromethane and aq. sodium bicarbonate. The organic layers are dried over sodium sulfate and concentrated. The solids remaining suspended in the aqueous layer are collected, washed with water, dried under reduced pressure, and combined with the solids obtained from concentration of the organic layers. The solids are taken up in dichloromethane and methanol with warming and filtered through a cotton plug to remove insolubles. The filtrate is then concentrated and the residue is crystallized from dichloromethane/hexane to give 0.0745 g of the title compound; mp 254-256° C.; MS m/z 403, 405; IR (mineral oil) 1413, 1235, 1597, 800, 1328 cm-1. 1H NMR (DMSOd6) δ2.64, 3.05, 3.69, 7.17, 7.25, 7.37, 7.55, 7.79, 7.84, 7.89, 7.96, 8.80.

Workup

  1. temperatureafter which it is cooled
  2. concentrationconcentrated under reduced pressure
  3. customThe residue is partitioned between dichloromethane and aq. sodium bicarbonate
  4. dry with materialThe organic layers are dried over sodium sulfate
  5. concentrationconcentrated
  6. customare collected
  7. washwashed with water
  8. customdried under reduced pressure
  9. customobtained from concentration of the organic layers
  10. filtrationfiltered through a cotton plug
  11. customto remove insolubles
  12. concentrationThe filtrate is then concentrated
  13. customthe residue is crystallized from dichloromethane/hexane

Sources & evidence

ORD record
ord-986b484036f2414b9a3fee803ba76049
Source dataset
uspto-grants-1999_06
Patent number
US05912246

Reaction notes

Loading…