3-Chloro-4-[2-(4-methylpiperidin-1-yl)ethyl]phenylamine → 3-(2-Chloro-4-trifluoromethylphenyl)propynoic acid-{3-chloro-4-[2-(4-methylpiperidin-1-yl)ethyl]phenyl}amide

HRID 735123Notes

Reaction equation

HRID 735123 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[C:12]#[C:13][C:14]([OH:16])=O.[Cl:17][C:18]1[CH:19]=[C:20]([NH2:33])[CH:21]=[CH:22][C:23]=1[CH2:24][CH2:25][N:26]1[CH2:31][CH2:30][CH:29]([CH3:32])[CH2:28][CH2:27]1>>[Cl:17][C:18]1[CH:19]=[C:20]([NH:33][C:14](=[O:16])[C:13]#[C:12][C:3]2[CH:4]=[CH:5][C:6]([C:8]([F:9])([F:10])[F:11])=[CH:7][C:2]=2[Cl:1])[CH:21]=[CH:22][C:23]=1[CH2:24][CH2:25][N:26]1[CH2:27][CH2:28][CH:29]([CH3:32])[CH2:30][CH2:31]1

Participants

3

Reactant 2

HCID 596916703-Chloro-4-[2-(4-methylpiperidin-1-yl)ethyl]phenylamineHCID 68817422(2-Chloro-4-trifluoromethylphenyl)propynoic acid

Product 1

HCID 578457873-(2-Chloro-4-trifluoromethylphenyl)propynoic acid-{3-chloro-4-[2-(4-methylpiperidin-1-yl)ethyl]phenyl}amide

Procedure

Prepared analogously to Example 2.3.f. from (2-chloro-4-trifluoromethylphenyl)propynoic acid and 3-chloro-4-[2-(4-methylpiperidin-1-yl)ethyl]phenylamine. Yield: 0.21 g (45.3% of theory); C24H23Cl2F3N2O (M=483.36); calc.: molecular ion peak (M+H)+: 483/485/487; found: molecular ion peak (M+H)+: 483/485/487; Rf value: 0.65 (Alox, petroleum ether/ethyl acetate (1:1)).

Workup

  1. customPrepared analogously to Example 2.3.f

Sources & evidence

ORD record
ord-5cac578e1f044238b63d7193696b0ff5
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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