Potassium Iodide → 1-[1-(4-fluorophenylmethyl)-1H-benzimidazol-2-yl]-5-[2-[4-(2-methoxycarbonylethyl)phenyl]ethyl]-1,5-diazacyclooctane

HRID 55327Notes

Reaction equation

HRID 55327 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]=[C:10]2[N:18]2[CH2:25][CH2:24][CH2:23][NH:22][CH2:21][CH2:20][CH2:19]2)=[CH:4][CH:3]=1.[CH3:26][O:27][C:28]([CH2:30][CH2:31][C:32]1[CH:40]=[CH:39][C:35]([CH2:36][CH2:37]Br)=[CH:34][CH:33]=1)=[O:29].C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>CN(C)C=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]=[C:10]2[N:18]2[CH2:25][CH2:24][CH2:23][N:22]([CH2:37][CH2:36][C:35]3[CH:39]=[CH:40][C:32]([CH2:31][CH2:30][C:28]([O:27][CH3:26])=[O:29])=[CH:33][CH:34]=3)[CH2:21][CH2:20][CH2:19]2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 199575114-(2-Methoxycarbonylethyl)phenethyl bromideHCID 199575511-[1-(4-fluorophenylmethyl)-1H-benzimidazol-2-yl]-1,5-diazacyclooctane

Product 1

HCID 199575241-[1-(4-fluorophenylmethyl)-1H-benzimidazol-2-yl]-5-[2-[4-(2-methoxycarbonylethyl)phenyl]ethyl]-1,5-diazacyclooctaneYield 61.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 1-[1-(4-fluorophenylmethyl)-1H-benzimidazol-2-yl]-1,5-diazacyclooctane (12.1 g) in N,N-dimethylformamide (70 ml) were added 4-(2-methoxycarbonylethyl)phenethyl bromide (9.49 g), sodium carbonate (3.71 g) and potassium iodide (0.58 g), and the mixture was heated at 100° C. for 1 hour. The reaction mixture was poured into an ice-water (200 ml), and the mixture was extracted with methylene chloride (200 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 1-[1-(4-fluorophenylmethyl)-1H-benzimidazol-2-yl]-5-[2-[4-(2-methoxycarbonylethyl)phenyl]ethyl]-1,5-diazacyclooctane (11.38 g) as a colorless oily liquid.

Workup

  1. extractionthe mixture was extracted with methylene chloride (200 ml)
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous MgSO4
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by medium pressure liquid column chromatography on a silica gel column
  6. additiona mixture of methylene chloride, diethyl ether and methanol (1:1:0.25) as eluent

Sources & evidence

ORD record
ord-312a7754477f4b8aade832d48ac82f79
Source dataset
uspto-grants-1997_04
Patent number
US05624948

Reaction notes

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