Benzylideneacetone → 3-(Aminomethyl)-6-methyl-4-phenyl-2(1H)-pyridinone

HRID 62360

Reaction equation

[NH2:1][CH2:2][C:3]1[C:4](=[O:13])[NH:5][C:6]([CH3:12])=[CH:7][C:8]=1[CH2:9][CH2:10][CH3:11].[C:14]1(/C=C/C(=O)C)[CH:19]=CC=C[CH:15]=1>>[NH2:1][CH2:2][C:3]1[C:4](=[O:13])[NH:5][C:6]([CH3:12])=[CH:7][C:8]=1[C:9]1[CH:19]=[CH:14][CH:15]=[CH:11][CH:10]=1

Participants

Reactant 2

HCID 637759Benzylideneacetone

HCID 671241403-(Aminomethyl)-6-methyl-4-propylpyridin-2(1H)-oneacetate2×

Product 1

HCID 671242923-(Aminomethyl)-6-methyl-4-phenyl-2(1H)-pyridinone

Procedure

The title compound was prepared in the same manner as described for 3-(aminomethyl)-6-methyl-4-propyl-2(1H)-pyridinone (Intermediate 5) using (3E)-4-phenyl-3-buten-2-one (20 g, 137 mmol). LCMS E-S (M+H)=215.0. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.2-12.3 (br s, 1H), 7.88-8.00 (br s, 3H), 7.43-7.51 (m, 3H), 7.29-7.38 (m, 2H), 6.08 (s, 1H), 3.67-3.70 (m, 2H), 2.23 (s, 3H).

Sources & evidence

ORD record: ord-db35674e3a784b24869104bdd40844d9
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09446041B2

Linked notes

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