4-Methylpiperidine → (E)-N-(4'-chlorobiphenyl-4-yl)-3-[4-(4-methylpiperidin-1-ylmethyl)phenyl]acrylamide

HRID 735170Notes

Reaction equation

HRID 735170 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]([CH:24]=O)=[CH:20][CH:19]=3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH3:27][CH:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1>ClCCl.CO>[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][N:31]4[CH2:32][CH2:33][CH:28]([CH3:27])[CH2:29][CH2:30]4)=[CH:20][CH:19]=3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 693814-MethylpiperidineHCID 86601892(E)-N-(4'-chlorobiphenyl-4-yl)-3-(4-formylphenyl)acrylamide

Product 1

HCID 57845736(E)-N-(4'-chlorobiphenyl-4-yl)-3-[4-(4-methylpiperidin-1-ylmethyl)phenyl]acrylamide

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Prepared analogously to Example 4.30.c. from (E)-N-(4′-chlorobiphenyl-4-yl)-3-(4-formylphenyl)acrylamide and 4-methylpiperidine. Yield: 80 mg (21.7% of theory); melting point: 207° C.-208° C.; C28H29ClN2O (M=445.00); calc.: molecular ion peak (M+H)+: 445/447; found: molecular ion peak (M+H)+: 445/447; Rf value: 0.76 (silica gel, dichloromethane/methanol (10:1)).

Workup

  1. customPrepared analogously to Example 4.30.c

Sources & evidence

ORD record
ord-62d2ebf3141543b2bc8041849d058a66
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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