Water → 2,6-Bis(2-methylphenyl)-1-methyl-4-piperidone

HRID 714204Notes

Reaction equation

HRID 714204 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]=[CH:9][C:10](=[O:20])[CH:11]=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19].[CH3:21][NH2:22].O>CN(C)C=O>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:9][C:10](=[O:20])[CH2:11][CH:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH3:19])[N:22]1[CH3:21]

Participants

5

Reactant 3

HCID 962WaterHCID 6329MethylamineHCID 45639421,5-Bis(2-methylphenyl)-1,4-pentadien-3-one

Product 1

HCID 695017532,6-Bis(2-methylphenyl)-1-methyl-4-piperidoneYield 52%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1,5-Bis(2-methylphenyl)-1, 4-pentadien-3-one (20ac, 0.50 g, 1.9 mmol) was dissolved in dimethyl formamide (10 ml). Methylamine (51, 1.0 ml, 11.6 mmol, 40% in water) was added and the mixture stirred for 24 hr at room temperature. The mixture was poured into water (50 ml) and stirred for 2 hr at room temperature. The resulting mixture was extracted into ethyl acetate, washed with saturated sodium chloride, dried over magnesium sulfate, filtered and evaporated to afford a solid. The crude solid was chromatographed on silica gel with ethyl acetate/hexane to afford a solid that was recrystallized from ethanol to give 0.29 g (52%) of a white solid: mp 155-157° C.; 1H NMR δ 1.82, (s, 3H), 2.40, (s, 6H), 2.44 (d, 2H, J=11.9 Hz), 2.77 (t, 2H, J=13.3 Hz), 3.74 (d, 2H, J=11.9 Hz), 7.16 (m, 6H), 7.67, (d, 2H, J=7.0 Hz); 13C NMR: δ 19.5, 39.9, 49.3, 65.8, 126.7, 126.9, 130.6, 134.8, 140.9, 207.2; Exact mass calcd for C20H23NO: 293.1779, observed (M+H) 294.1856.

Workup

  1. stirringstirred for 2 hr at room temperature
  2. extractionThe resulting mixture was extracted into ethyl acetate
  3. washwashed with saturated sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customto afford a solid
  8. customThe crude solid was chromatographed on silica gel with ethyl acetate/hexane
  9. customto afford a solid
  10. customthat was recrystallized from ethanol

Sources & evidence

ORD record
ord-08a5630004974cfcbfab67a0fe341081
Source dataset
uspto-grants-2015_11
Patent number
US09187397B2

Reaction notes

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