4-(Piperidin-1-ylmethyl)aniline → 3-(3-chlorobiphenyl-4-yl)propynoic acid-(4-piperidin-1-ylmethylphenyl)amide Hydrochloride

HRID 735064Notes

Reaction equation

HRID 735064 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:5]=[CH:6][C:7]=1[C:8]#[C:9][C:10]([OH:12])=O.[N:19]1([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([NH2:32])=[CH:28][CH:27]=2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.ClCCl.CO.N>>[ClH:1].[N:19]1([CH2:25][C:26]2[CH:27]=[CH:28][C:29]([NH:32][C:10](=[O:12])[C:9]#[C:8][C:7]3[CH:6]=[CH:5][C:4]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)=[CH:3][C:2]=3[Cl:1])=[CH:30][CH:31]=2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

4

Reactant 3

HCID 8461504-(Piperidin-1-ylmethyl)anilineHCID 21584172Ammonia methanol dichloromethaneHCID 68818528(3-chlorobiphenyl-4-yl)propynoic Acid

Product 1

HCID 688184153-(3-chlorobiphenyl-4-yl)propynoic acid-(4-piperidin-1-ylmethylphenyl)amide Hydrochloride

Procedure

Prepared analogously to Example 3.8 from (3-chlorobiphenyl-4-yl)propynoic acid and 4-piperidin-1-ylmethylphenylamine. Yield: 0.35 g (75% of theory); melting point: 260° C.-265° C.; C27H25ClN20*HCl (M=465.41); calc.: molecular ion peak (M+H)+: 429/31 (Cl); found: molecular ion peak (M+H)+: 429/31 (Cl); Rf value: 0.6 (silica gel, dichloromethane/methanol/ammonia (90:10:0.1)).

Sources & evidence

ORD record
ord-d3b5aeaa5b6a4f9c8e3fff2998e3e4ba
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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