Water → 1-Methyl-2,6-diphenylpiperidin-4-one

HRID 77686

반응식

HRID 77686 반응식
[C:1]1([CH:7]=[CH:8][C:9](=[O:18])[CH:10]=[CH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:19][NH2:20].O>CN(C)C=O>[C:1]1([CH:7]2[CH2:8][C:9](=[O:18])[CH2:10][CH:11]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:20]2[CH3:19])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 6329MethylamineHCID 95417Dibenzylidene acetone

생성물 1

HCID 2807081-Methyl-2,6-diphenylpiperidin-4-one수율 60.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

1,5-Diphenyl-1,4-pentadien-3-one (20b, 4.00 g, 17.1 mmol) was dissolved in dimethyl formamide (60 ml). Methylamine (51, 6.0 ml, 70.0 mmol, 40% in water) was added and the mixture stirred for 96 hr at room temperature. The mixture was poured into water (250 ml) and stirred for 1 hr at room temperature. The resulting mixture was extracted into ethyl ether, washed with saturated sodium chloride, dried over magnesium sulfate, filtered and evaporated to afford a solid. The crude solid was recrystallized from ethanol to give 2.74 g (60%) of a white solid: mp 147-149° C. [expected mp 148-150° C.]; 1H NMR δ 1.82 (s, 3H), 2.50, (dd, 2H, J=12.3, 2.5 Hz), 2.82 (t, 2H, J=13.3 Hz), 3.45 (dd, 2H, J=12.9, 2.4 Hz), 7.34, (m, 10H); 13C NMR: δ 40.8, 50.8, 70.2, 127.0, 127.6, 128.8, 143.1, 206.8.

후처리

  1. stirringstirred for 1 hr at room temperature
  2. extractionThe resulting mixture was extracted into ethyl ether
  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 recrystallized from ethanol

출처 및 근거

ORD 기록
ord-8d5f91124d8d4b2d91d969bdc27243d3
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841326B2

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