18-Crown-6 → 2-[3-(3-Ethyl-2-oxo-azepan-3-yl)-phenoxy]-4-imidazol-1-ylmethyl-benzonitrile

HRID 1594858

Reaction equation

HRID 1594858 reaction equation
F[C:2]1[CH:9]=[C:8]([CH2:10][N:11]2[CH:15]=[CH:14][N:13]=[CH:12]2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH2:16]([C:18]1([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([OH:32])[CH:27]=2)[CH2:24][CH2:23][CH2:22][CH2:21][NH:20][C:19]1=[O:25])[CH3:17].[F-].[K+].C1OCCOCCOCCOCCOCCOC1>CC#N>[CH2:16]([C:18]1([C:26]2[CH:27]=[C:28]([CH:29]=[CH:30][CH:31]=2)[O:32][C:2]2[CH:9]=[C:8]([CH2:10][N:11]3[CH:15]=[CH:14][N:13]=[CH:12]3)[CH:7]=[CH:6][C:3]=2[C:4]#[N:5])[CH2:24][CH2:23][CH2:22][CH2:21][NH:20][C:19]1=[O:25])[CH3:17]

Participants

6

Reactant 4

HCID 2855718-Crown-6HCID 522689Potassium FluorideHCID 21697068Benzonitrile, 2-fluoro-4-(1H-imidazol-1-ylmethyl)-HCID 21706219HCID 21706219, compound

Product 1

HCID 110370902-[3-(3-Ethyl-2-oxo-azepan-3-yl)-phenoxy]-4-imidazol-1-ylmethyl-benzonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Fluoro-4-imidazol-1-ylmethyl-benzonitrile (as described in Example 1, Step E) (0.065 g, 0.325 mmol), 3-ethyl-3-(3-hydroxy-phenyl)-azepan-2-one (as described in Step B above) (0.076 g, 0.325 mmol), KF.Al2O3 (0.091 g) and 18-Crown-6 (0.008 g, 0.030 mmol) were refluxed in CH3CN (8 mL) under Ar for 72 h. The solution was filtered, concentrated in vacuo, and purified using SiO2 chromatography (0.5-3.0% MeOH/CH2Cl2). The compound was treated with 1N HCl ethereal solution to give the title compound.

Workup

  1. filtrationThe solution was filtered
  2. concentrationconcentrated in vacuo
  3. custompurified
  4. additionThe compound was treated with 1N HCl ethereal solution

Sources & evidence

ORD record
ord-9098ffd1b25046b9878da1ffb307ece8
Source dataset
uspto-grants-2001_09
Patent number
US06284755B1

Linked notes

Loading…