Potassium Iodide → HCID 22037021, compound

HRID 1790007Notes

Reaction equation

HRID 1790007 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]2[N:12]([CH2:13][C:14]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[N:17]=[CH:16][CH:15]=3)[C:11]3[CH:24]=[CH:25][CH:26]=[CH:27][C:10]=3[N:9]=2)[CH2:3][CH2:2]1.Cl[CH2:29][C:30]#[N:31].[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CC(C)CC(=O)C.O>[N:17]1[C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:14]([CH2:13][N:12]2[C:11]3[CH:24]=[CH:25][CH:26]=[CH:27][C:10]=3[N:9]=[C:8]2[NH:7][CH:4]2[CH2:3][CH2:2][N:1]([CH2:29][C:30]#[N:31])[CH2:6][CH2:5]2)=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 22037006HCID 22037006, compound

Product 1

HCID 22037021HCID 22037021, compoundYield 18.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of N-(4-piperidinyl)-1-(4-quinolinylmethyl)-1H-benzimidazol-2-amine (comp. 23) (0.0129 mol), chloroacetonitrile (0.0155 mol), potassium iodide (0.00129 mol) and potassium carbonate (0.0258 mol) in 4-methyl-2-pentanone (80 ml) was stirred and refluxed for 5 hours. H2O was added. The solvent was evaporated. H2O and CH2Cl2 were added. The precipitate was filtered off. The filtrate was separated into its layers. The organic layer was dried (MgSO4), filtered and the solvent was evaporated. The residue (3.5 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/N OH 95/5/0.3; 1540 em). The pure fractions were collected and the solvent was evaporated. The residue was crystallized from CH3CN. The precipitate was filtered off and dried, yielding 0.94 g 4-[[1-(4-quinolinylmethyl)1H-benzimidazol-2-yl]amino]-1-piperidineacetonitrile; mp. 190° C. (interm. 41).

Workup

  1. temperaturerefluxed for 5 hours
  2. customThe solvent was evaporated
  3. additionH2O and CH2Cl2 were added
  4. filtrationThe precipitate was filtered off
  5. customThe filtrate was separated into its layers
  6. dry with materialThe organic layer was dried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent was evaporated
  9. customThe residue (3.5 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/N OH 95/5/0.3; 1540 em)
  10. customThe pure fractions were collected
  11. customthe solvent was evaporated
  12. customThe residue was crystallized from CH3CN
  13. filtrationThe precipitate was filtered off
  14. customdried

Sources & evidence

ORD record
ord-777e8d975bae46508dbc8e95dcfff963
Source dataset
uspto-grants-2006_07
Patent number
US07071192B1

Reaction notes

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