Potassium Iodide → HCID 15037477, compound

HRID 704727Notes

Reaction equation

HRID 704727 reaction equation
Br[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[F:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][N:18]2[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[N:20]=[C:19]2[NH:27][CH:28]2[CH2:32][CH2:31][NH:30][CH2:29]2)=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>O.CN(C)C=O>[F:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][N:18]2[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[N:20]=[C:19]2[NH:27][CH:28]2[CH2:32][CH2:31][N:30]([CH2:2][CH2:3][C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH2:29]2)=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 7666Phenethyl bromideHCID 10340Sodium CarbonateHCID 15037382HCID 15037382, compound

Product 1

HCID 15037477HCID 15037477, compoundYield 12%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 1.85 parts of (2-bromoethyl)benzene, 3.1 parts of 1-[(4-fluorophenyl)methyl]-N-(3-pyrrolidinyl)-1H-benzimidazol-2-amine, 1.06 parts of sodium carbonate, 0.1 parts of potassium iodide and 120 parts of N,N-dimethylformamide was stirred and heated overnight at 70° C. The reaction mixture was poured into water and 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 (96:4 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from 2,2'-oxybispropane. The product was filtered off and dried, yielding 0.5 parts (12%) of 1-[(4-fluorophenyl)methyl]-N-[1(2-phenylethyl)-3-pyrrolidinyl]-1H-benzimidazol-2-amine; mp. 126.1° C. (compound 127).

Workup

  1. extractionthe product was extracted with 4-methyl-2-pentanone
  2. customThe extract was dried
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by column chromatography over silica gel using
  6. additiona mixture of trichloromethane and methanol (96:4 by volume) as eluent
  7. customThe pure fractions were collected
  8. customthe eluent was evaporated
  9. customThe residue was crystallized from 2,2'-oxybispropane
  10. filtrationThe product was filtered off
  11. customdried

Sources & evidence

ORD record
ord-9df09c8eda6f4141b6ff9d0a98a5380f
Source dataset
uspto-grants-1991_01
Patent number
US04988689

Reaction notes

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