4-Methylmorpholine → N-[2-(3-cyanophenoxy)ethyl]-4-cyanobenzamide

HRID 747658Notes

Reaction equation

HRID 747658 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][CH:4]=1)#[N:2].CN1CCOCC1.ClC(OCC)=O.[NH2:25][CH2:26][CH2:27][O:28][C:29]1[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=1)[C:32]#[N:33]>CN(C)C=O.C(OCC)(=O)C>[C:32]([C:31]1[CH:30]=[C:29]([CH:36]=[CH:35][CH:34]=1)[O:28][CH2:27][CH2:26][NH:25][C:7](=[O:9])[C:6]1[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:11][CH:10]=1)#[N:33]

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 10928Ethyl chloroformateHCID 120874-Cyanobenzoic acidHCID 109098773-(2-Aminoethoxy)benzonitrile

Product 1

HCID 11066232N-[2-(3-cyanophenoxy)ethyl]-4-cyanobenzamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.13 g (7.68 mmol) of 4-cyanobenzoic acid and 1.6 ml (14.1 mmol) of N-methylmorpholine were dissolved in 30 ml of dimethylformamide. 0.67 ml (7.05 mmol) of ethyl chloroformate was added to the solution under cooling with ice/water. After stirring for 5 minutes, 1.27 g (6.41 mmol) of 3-(2-aminoethoxy)benzonitrile was added to the reaction mixture, and the obtained mixture was stirred at room temperature for one hour. After the treatment with ethyl acetate as the extractant in an ordinary manner, the title compound was obtained.

Workup

  1. stirringthe obtained mixture was stirred at room temperature for one hour

Sources & evidence

ORD record
ord-437a3928bfc14457a81bb047c2de8364
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

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