Sodium Bicarbonate → 5-[2-[4-(2-ethoxycarbonylethyl)phenyl]ethyl]-1-[1-(4-fluorophenylmethyl)-1H-benzimidazol-2-yl]-1,5-diazacyclooctane

HRID 55330Notes

Reaction equation

HRID 55330 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.[CH2:19]([O:21][C:22]([CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][CH2:33][N:34]2[CH2:41][CH2:40][CH2:39][NH:38][CH2:37][CH2:36][CH2:35]2)=[CH:28][CH:27]=1)=[O:23])[CH3:20].C([O-])(O)=O.[Na+]>C(O)CCC>[CH2:19]([O:21][C:22]([CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][CH2:33][N:34]2[CH2:35][CH2:36][CH2:37][N:38]([C:2]3[N:6]([CH2:7][C:8]4[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=4)[C:5]4[CH:15]=[CH:16][CH:17]=[CH:18][C:4]=4[N:3]=3)[CH2:39][CH2:40][CH2:41]2)=[CH:28][CH:27]=1)=[O:23])[CH3:20]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 199575251-[2-[4-(2-Ethoxycarbonylethyl)phenyl]ethyl]-1,5-diazacyclooctaneHCID 199575402-Bromo-1-[(4-fluorophenyl)methyl]-1H-benzimidazole

Product 1

HCID 199575285-[2-[4-(2-ethoxycarbonylethyl)phenyl]ethyl]-1-[1-(4-fluorophenylmethyl)-1H-benzimidazol-2-yl]-1,5-diazacyclooctaneYield 85%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

To a solution of 2-bromo-1-(4-fluorophenylmethyl)-1H-benzimidazole (0.244 g) in n-butanol (1 ml) was added 1-[2-[4-(2-ethoxycarbonylethyl)phenyl]ethyl]-1,5-diazacyclooctane (1.00 g), and the mixture was refluxed for 2 hours. To the reaction mixture was added a saturated aqueous NaHCO3 solution (50 ml), and the mixture was extracted with methylene chloride (30 ml). The extract was washed with water, and dried over anhydrous MgSO4. The solvent was removed under reduced pressure, and the residue was purified by medium pressure liquid column chromatography on a silica gel column using a mixture of methylene chloride, diethyl ether and methanol (1:1:0.25) as eluent to give a mixture (0.369 g) of 5-[2-[4-(2-ethoxycarbonylethyl)phenyl]ethyl]-1-[1-(4-fluorophenylmethyl)-1H-benzimidazol-2-yl]-1,5-diazacyclooctane and 5-[2-[4-(2-n-butoxycarbonylethyl)phenyl]ethyl]-1-[1-(4-fluorophenylmethyl)-1H-benzimidazol-2-yl]-1,5-diazacyclooctane.

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. extractionthe mixture was extracted with methylene chloride (30 ml)
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous MgSO4
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by medium pressure liquid column chromatography on a silica gel column
  7. additiona mixture of methylene chloride, diethyl ether and methanol (1:1:0.25) as eluent

Sources & evidence

ORD record
ord-f99f3708ffbd4d07b06b88d0ac6b5bc9
Source dataset
uspto-grants-1997_04
Patent number
US05624948

Reaction notes

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