{4-[2-(Diethylamino)ethoxy]phenyl}methanamine → 3-(2-Chloro-4-methylphenyl)propynoic acid-[4-(2-diethylaminoethoxy)phenyl]methylamide

HRID 735068Notes

Reaction equation

HRID 735068 reaction equation
[CH2:1]([N:3]([CH2:15][CH3:16])[CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][NH2:14])=[CH:9][CH:8]=1)[CH3:2].[Cl:17][C:18]1[CH:23]=[C:22]([C:24](F)(F)F)[CH:21]=[CH:20][C:19]=1[C:28]#[C:29][C:30](O)=[O:31]>ClCCl.CO>[CH2:15]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:13][NH:14][C:30](=[O:31])[C:29]#[C:28][C:19]2[CH:20]=[CH:21][C:22]([CH3:24])=[CH:23][C:18]=2[Cl:17])=[CH:11][CH:12]=1)[CH3:16]

Participants

4

Reactant 2

HCID 235944{4-[2-(Diethylamino)ethoxy]phenyl}methanamineHCID 68817422(2-Chloro-4-trifluoromethylphenyl)propynoic acid

Product 1

HCID 688161963-(2-Chloro-4-methylphenyl)propynoic acid-[4-(2-diethylaminoethoxy)phenyl]methylamide

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Prepared analogously to Example 2.3.f. from [4-(2-diethylaminoethoxy)phenyl]methylamine and (2-chloro-4-trifluoromethylphenyl)propynoic acid. Yield: 60 mg (22% of theory); melting point: 135° C.-138° C.; C23H24ClF3N2O2 (M=452.90); calc.: molecular ion peak (M+H)+: 453/455; found: molecular ion peak (M+H)+: 453/455; Rf value: 0.4 (silica gel, dichloromethane/methanol (9:1)).

Workup

  1. customPrepared analogously to Example 2.3.f

Sources & evidence

ORD record
ord-00ab607748f4433d9ace12dca0689b73
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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