1,5-Diazocane → 1-[1-(4-fluorophenylmethyl)-1H-benzimidazol-2-yl]-1,5-diazacyclooctane

HRID 55317Notes

Reaction equation

HRID 55317 reaction equation
Br[C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)[C:5]2[CH:15]=[CH:16][CH:17]=[CH:18][C:4]=2[N:3]=1.[NH:19]1[CH2:26][CH2:25][CH2:24][NH:23][CH2:22][CH2:21][CH2:20]1>>[F:14][C:11]1[CH:12]=[CH:13][C:8]([CH2:7][N:6]2[C:5]3[CH:15]=[CH:16][CH:17]=[CH:18][C:4]=3[N:3]=[C:2]2[N:19]2[CH2:26][CH2:25][CH2:24][NH:23][CH2:22][CH2:21][CH2:20]2)=[CH:9][CH:10]=1

Participants

3

Reactant 2

HCID 52483731,5-DiazocaneHCID 199575402-Bromo-1-[(4-fluorophenyl)methyl]-1H-benzimidazole

Product 1

HCID 199575511-[1-(4-fluorophenylmethyl)-1H-benzimidazol-2-yl]-1,5-diazacyclooctaneYield 108.3%

Conditions

Temperature
80 °C

Procedure

A mixture of 2-bromo-1-(4-fluorophenylmethyl)-1H-benzimidazole (10.07 g) and 1,5-diazacyclooctane (5.60 g) was heated at 80° C. for 1 hour. To the reaction mixture was added distilled water (300 ml), and the mixture was extracted with methylene chloride (300 ml). The extract was washed with water, and dried over anhydrous MgSO4. The solvent was removed under reduced pressure to give 1-[1-(4-fluorophenylmethyl)-1H-benzimidazol-2-yl]-1,5-diazacyclooctane (12.1 g) as a colorless oily liquid.

Workup

  1. additionTo the reaction mixture was added
  2. distillationdistilled water (300 ml)
  3. extractionthe mixture was extracted with methylene chloride (300 ml)
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous MgSO4
  6. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-34a5a9d5c3fc4b3aa2bbca2d61d97570
Source dataset
uspto-grants-1997_04
Patent number
US05624948

Reaction notes

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