3,4-Dimethoxyphenol → N-cyclohexyl-N-cyclopentyl-4-(3,4-dimethoxyphenoxy)benzamide

HRID 1588900Notes

Reaction equation

HRID 1588900 reaction equation
[CH:1]1([N:6]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[C:7](=[O:15])[C:8]2[CH:13]=[CH:12][C:11](Br)=[CH:10][CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:22][O:23][C:24]1[CH:25]=[C:26]([OH:32])[CH:27]=[CH:28][C:29]=1[O:30][CH3:31]>N1C(C)=CC(C)=CC=1C>[CH:16]1([N:6]([CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[C:7](=[O:15])[C:8]2[CH:13]=[CH:12][C:11]([O:32][C:26]3[CH:27]=[CH:28][C:29]([O:30][CH3:31])=[C:24]([O:23][CH3:22])[CH:25]=3)=[CH:10][CH:9]=2)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

4

Reactant 2

HCID 162513,4-DimethoxyphenolHCID 197548884-bromo-N-cyclohexyl-N-cyclopentylbenzamide

Product 1

HCID 19754862N-cyclohexyl-N-cyclopentyl-4-(3,4-dimethoxyphenoxy)benzamide

Reagents, catalysts & solvents 1

HCID 79532,4,6-TrimethylpyridineSolvent

Procedure

The reaction and workup were carried out in the same manner as described in Example 1 using p-bromobenzoic acid N-cyclopentyl-N-cyclohexyl amide (2.350 g, 6.71 mmol), 3,4-dimethoxy phenol (1.051 g, 6.81mmol) and cuprous oxide (478 mg, 3.34 mmol) in 2,4,6-collidine (15 ml). The crude product was chromatographed on silica gel using mixtures of ethyl acetate and hexane as eluents to give the title compound as a crystalline solid that could be recrystallized from ethyl acetate and hexane, m. pt. 153.96° C. (DSC).

Workup

  1. customThe reaction and workup
  2. customThe crude product was chromatographed on silica gel using mixtures of ethyl acetate and hexane as eluents

Sources & evidence

ORD record
ord-758f24e7bbd645829ecd3aeae471fded
Source dataset
uspto-grants-1993_06
Patent number
US05223539

Reaction notes

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