4-(2,6-Dimethyl-piperidin-1-ylmethyl)-phenylamine → 3-(4'-Chlorobiphenyl-4-yl)propynoic acid-[4-(2,6-dimethylpiperidin-1-ylmethyl)phenyl]amide

HRID 735044Notes

Reaction equation

HRID 735044 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[C:15][C:16]([OH:18])=O)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH3:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH:22]([CH3:26])[N:21]1[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([NH2:34])=[CH:30][CH:29]=1>ClCCl>[CH3:26][CH:22]1[CH2:23][CH2:24][CH2:25][CH:20]([CH3:19])[N:21]1[CH2:27][C:28]1[CH:29]=[CH:30][C:31]([NH:34][C:16](=[O:18])[C:15]#[C:14][C:11]2[CH:10]=[CH:9][C:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)=[CH:13][CH:12]=2)=[CH:32][CH:33]=1

Participants

4

Reactant 2

HCID 31539974-(2,6-Dimethyl-piperidin-1-ylmethyl)-phenylamineHCID 68816492(4'-Chlorobiphenyl-4-yl)propynoic acid

Product 1

HCID 578457383-(4'-Chlorobiphenyl-4-yl)propynoic acid-[4-(2,6-dimethylpiperidin-1-ylmethyl)phenyl]amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Prepared analogously to Example 3.8. from (4′-chlorobiphenyl-4-yl)propynoic acid and 4-(2,6-dimethylpiperidin-1-ylmethyl)phenylamine. Yield: 100 mg (22% of theory); melting point: 158° C.-163° C.; C29H29ClN2O (M=457.01); calc.: molecular ion peak (M+H)+: 458/460 (Cl); found: molecular ion peak (M+H)+: 458/460 (Cl); Rf value: 0.50 (silica gel, dichloromethane/methanolic ammonia (90:10:0.1)).

Workup

  1. customPrepared analogously to Example 3.8

Sources & evidence

ORD record
ord-97362844f1464d7abdb90a9b7aba13bc
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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