4'-Butylaminomethyl-2-cyanobiphenyl → 4-carboxy-4-ethyl-hexanoic acid N-butyl-N-(2'-cyanobiphenyl-4-ylmethyl)-amide

HRID 2380679Notes

Reaction equation

HRID 2380679 reaction equation
[CH2:1]([NH:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]#[N:20])=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH3:4].[CH2:21]([C:23]1([CH2:31][CH3:32])[CH2:29][CH2:28][C:27](=[O:30])[O:26][C:24]1=[O:25])[CH3:22]>O1CCOCC1>[CH2:1]([N:5]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]#[N:20])=[CH:9][CH:8]=1)[C:27](=[O:30])[CH2:28][CH2:29][C:23]([C:24]([OH:26])=[O:25])([CH2:31][CH3:32])[CH2:21][CH3:22])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 153383534'-Butylaminomethyl-2-cyanobiphenylHCID 217514313,3-Diethyloxane-2,6-dione

Product 1

HCID 541712894-carboxy-4-ethyl-hexanoic acid N-butyl-N-(2'-cyanobiphenyl-4-ylmethyl)-amide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The starting material can be prepared, for example, as follows: A solution of 3.2 g of N-butyl-N-(2'-cyanobiphenyl-4-ylmethyl)-amine and 3.09 g of 2,2-diethylglutaric acid anhydride in 50 ml of dioxane is heated at 115° (bath temperature) for 6 hours. After concentration of the reaction mixture by evaporation, the residue is taken up in 100 ml of ethyl acetate, and the ethyl acetate phase is washed twice with 50 ml of water each time, dried over Na2SO4 and concentrated by evaporation in vacuo. Chromatography of the evaporation residue on silica gel 60 (40-63 μm) using CH2Cl2 /CH3OH (95:5) as eluant yields pure 4-carboxy-4-ethyl-hexanoic acid N-butyl-N-(2'-cyanobiphenyl-4-ylmethyl)-amide that has an Rf value of 0.72 [CH2Cl2 /CH3OH (4:1)].

Workup

  1. customAfter concentration of the reaction mixture by evaporation
  2. washthe ethyl acetate phase is washed twice with 50 ml of water each time
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated by evaporation in vacuo

Sources & evidence

ORD record
ord-3937e5a35dc3458d80f1b4921c1183ee
Source dataset
uspto-grants-1994_11
Patent number
US05369110

Reaction notes

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