Potassium Iodide → HCID 13769681, compound

HRID 979932Notes

Reaction equation

HRID 979932 reaction equation
Br[C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[F:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][N:15]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[N:17]=[C:16]2[NH:24][CH:25]2[CH2:30][CH2:29][N:28]([CH2:31][CH2:32][NH:33][CH3:34])[CH2:27][CH2:26]2)=[CH:10][CH:9]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>CN(C)C(=O)C>[F:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][N:15]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[N:17]=[C:16]2[NH:24][CH:25]2[CH2:30][CH2:29][N:28]([CH2:31][CH2:32][N:33]([CH3:34])[C:2]3[S:3][CH:4]=[CH:5][N:6]=3)[CH2:27][CH2:26]2)=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 764302-BromothiazoleHCID 13588080HCID 13588080, compound

Product 1

HCID 13769681HCID 13769681, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 2.5 parts of 2-bromothiazole, 5.72 parts of 1-[(4-fluorophenyl)methyl]-N-[1-[2-(methylamino)ethyl]-4-piperidinyl]-1H-benzimidazol-2-amine, 1.6 parts of sodium carbonate, 0.1 parts of potassium iodide and 27 parts of N,N-dimethylacetamide was stirred and heated overnight at 140° C. The reaction mixture was poured onto water. The product was extracted with 4-methyl-2-pentanone. The extract was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from 1,1'-oxybisethane, yielding 3.5 parts (50%) of 1-[(4-fluorophenyl)methyl]-N-[1-[2-[methyl(2-thiazolyl)amino]ethyl]-4-piperidinyl]-1H-benzimidazol-2-amine; mp. 143.2° C. (compound 50).

Workup

  1. additionThe reaction mixture was poured onto water
  2. extractionThe product was extracted with 4-methyl-2-pentanone
  3. customThe extract was dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography over silica gel using
  7. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  8. customThe pure fractions were collected
  9. customthe eluent was evaporated
  10. customThe residue was crystallized from 1,1'-oxybisethane

Sources & evidence

ORD record
ord-2a00da21286d422fac3561152c9ee51b
Source dataset
uspto-grants-1987_01
Patent number
US04634704

Reaction notes

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