4-(Piperidin-1-ylmethyl)aniline → 3-[5-(4-Chlorophenyl)pyridin-2-yl]propynoic acid-(4-piperidin-1-ylmethylphenyl)amide

HRID 735059Notes

Reaction equation

HRID 735059 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([C:14]#[C:15][C:16]([OH:18])=O)=[N:12][CH:13]=2)=[CH:4][CH:3]=1.[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>>[N:19]1([CH2:25][C:26]2[CH:27]=[CH:28][C:29]([NH:32][C:16](=[O:18])[C:15]#[C:14][C:11]3[CH:10]=[CH:9][C:8]([C:5]4[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=4)=[CH:13][N:12]=3)=[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 68816808[5-(4-chlorophenyl)pyridin-2-yl]propynoic Acid

Product 1

HCID 578457333-[5-(4-Chlorophenyl)pyridin-2-yl]propynoic acid-(4-piperidin-1-ylmethylphenyl)amide

Procedure

Prepared analogously to Example 2.3.f. from [5-(4-chlorophenyl)pyridin-2-yl]propynoic acid and 4-piperidin-1-ylmethylphenylamine. Yield: 0.2 g (48% of theory); C26H24ClN3O (M=429.95); calc.: molecular ion peak (M+H)+: 430/432; found: molecular ion peak (M+H)+: 430/432; Rf value: 0.4 (silica gel, dichloromethane/methanol/ammonia (90:10:0.1)).

Workup

  1. customPrepared analogously to Example 2.3.f

Sources & evidence

ORD record
ord-50c0ba4403af49afa7380d202aae99ee
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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