rel-(3R,5S)-3,5-Dimethylpiperidine → (E)-N-(4'-chlorobiphenyl-4-yl)-3-[4-(cis-3,5-dimethylpiperidin-1-ylmethyl)phenyl]acrylamide

HRID 735173Notes

Reaction equation

HRID 735173 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:26])/[CH:16]=[CH:17]/[C:18]3[CH:23]=[CH:22][C:21]([CH2:24]Cl)=[CH:20][CH:19]=3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH3:27][C@H:28]1[CH2:33][C@@H:32]([CH3:34])[CH2:31][NH:30][CH2:29]1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:26])/[CH:16]=[CH:17]/[C:18]3[CH:19]=[CH:20][C:21]([CH2:24][N:30]4[CH2:31][C@H:32]([CH3:34])[CH2:33][C@H:28]([CH3:27])[CH2:29]4)=[CH:22][CH:23]=3)=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 641101rel-(3R,5S)-3,5-DimethylpiperidineHCID 68816418(E)-N-(4'-chlorobiphenyl-4-yl)-3-(4-chloromethylphenyl)acrylamide

Product 1

HCID 57845848(E)-N-(4'-chlorobiphenyl-4-yl)-3-[4-(cis-3,5-dimethylpiperidin-1-ylmethyl)phenyl]acrylamide

Procedure

Prepared analogously to Example 1.2.c. from (E)-N-(4′-chlorobiphenyl-4-yl)-3-(4-chloromethylphenyl)acrylamide and cis-3,5-dimethylpiperidine. Yield: 30 mg (30% of theory); melting point: 217° C.-218° C.; C29H31ClN2O (M=459.03); calc.: molecular ion peak (M+H)+: 459/461; found: molecular ion peak (M+H)+: 459/461.

Workup

  1. customPrepared analogously to Example 1.2.c

Sources & evidence

ORD record
ord-59c47cfa923747aba9de140bd5e6df9a
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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