Propanal → 3-(2,4-Dimethylphenyl)-5-(dipropylamino)-1-methylpyridin-2(1H)-one

HRID 598055Notes

Reaction equation

HRID 598055 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][C:11]=2[CH3:17])[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.[CH:18](=O)[CH2:19][CH3:20].C(O[BH-](O[C:32](=O)[CH3:33])OC(=O)C)(=O)C.[Na+].Cl[CH2:37]Cl>>[CH3:17][C:11]1[CH:12]=[C:13]([CH3:16])[CH:14]=[CH:15][C:10]=1[C:4]1[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=[C:2]([N:1]([CH2:37][CH2:32][CH3:33])[CH2:18][CH2:19][CH3:20])[CH:3]=1

Participants

5

Reactant 4

HCID 527PropanalHCID 6344Dichloromethane2×HCID 5049666Sodium triacetoxyborohydrideHCID 672669435-Amino-3-(2,4-dimethylphenyl)-1-methylpyridin-2(1H)-one

Product 1

HCID 589386273-(2,4-Dimethylphenyl)-5-(dipropylamino)-1-methylpyridin-2(1H)-oneYield 100%

Conditions

Temperature
25 °C

Procedure

To a solution containing 0.063 g (0.27 mmol) of 5-amino-3-(2,4-dimethylphenyl)-1-methylpyridin-2(1H)-one in 20 ml of dichloromethane was added 0.060 ml (0.83 mmol) of propionaldehyde followed by 0.20 g (0.94 mmol) of sodium triacetoxyborohydride under a nitrogen atmosphere. The reaction was allowed to stir at 25° C. overnight. The reaction was diluted with dichloromethane and washed with saturated sodium bicarbonate. The organic phase was dried over magnesium sulfate. Filtration, removal of solvent and purification of the residue via biotage eluting with ethyl acetate gave 0.088 g (100%) of product.

Workup

  1. washwashed with saturated sodium bicarbonate
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. filtrationFiltration, removal of solvent and purification of the residue via biotage
  4. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-12f5a822b53a4118b4f0ef2b4903652f
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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