2-Chlorobenzimidazole → HCID 86585568, compound

HRID 380382Notes

Reaction equation

HRID 380382 reaction equation
[Cl:1][C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1.[CH3:11][N:12]1[C:20]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:14]2[CH2:21][N:22]([CH2:25][CH2:26][CH2:27][NH2:28])[CH2:23][CH2:24][C:13]1=2>C(Cl)(Cl)Cl.[Cu]>[ClH:1].[ClH:1].[NH:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=[C:2]1[NH:28][CH2:27][CH2:26][CH2:25][N:22]1[CH2:23][CH2:24][C:13]2[N:12]([CH3:11])[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[C:14]=2[CH2:21]1

Participants

5

Reactant 2

HCID 785722-ChlorobenzimidazoleHCID 18677412HCID 18677412, compound

Product 1

HCID 86585568HCID 86585568, compoundYield 33.9%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 6212ChloroformSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 2-chloro-1H-benzimidazole (0.015 mol), intermediate 16 (0.015 mol) and copper (0.015 mol) was stirred in an oil bath at 180° C. The mixture was cooled and the product was dissolved in CHCl3 (50 ml). The solution was filtered over dicalite and the filtrate was evaporated. The residue was purified by column chromatography over silica gel (eluent: CHCl3/(CH3OH/NH3) 95/5). The pure fractions were collected and the solvent was evaporated. The residue was dissolved in CH3CN (50 ml) and converted into the hydrochloric acid salt (1:2) with HCl/2-propanol. The salt was filtered off, washed on filter with cold CH3CN (20 ml), then dried, yielding 1.1 g (17%) of N-1H-benzimidazol-2-yl-1,3,4,5-tetrahydro-5-methyl-2H-pyrido [4,3-b]indole-2-propanamine dihydrochloride.hemihydrate (compound 105).

Workup

  1. temperatureThe mixture was cooled
  2. filtrationThe solution was filtered over dicalite
  3. customthe filtrate was evaporated
  4. customThe residue was purified by column chromatography over silica gel (eluent: CHCl3/(CH3OH/NH3) 95/5)
  5. customThe pure fractions were collected
  6. customthe solvent was evaporated
  7. dissolutionThe residue was dissolved in CH3CN (50 ml)
  8. filtrationThe salt was filtered off
  9. washwashed
  10. filtrationon filter with cold CH3CN (20 ml)
  11. customdried

Sources & evidence

ORD record
ord-f506014a3c694c8da424af66248dc33d
Source dataset
uspto-grants-2001_10
Patent number
US06303614B1

Reaction notes

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