4'-Fluoroacetophenone → 1-(4-{4-[(1-Cyclobutyl-4-piperidinyl)methyl]-1-piperidinyl}phenyl)ethanone

HRID 1869642노트

반응식

HRID 1869642 반응식
[CH:1]1([N:5]2[CH2:10][CH2:9][CH:8]([CH2:11][CH:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.[CH3:18][C:19]([C:21]1[CH:26]=[CH:25][C:24](F)=[CH:23][CH:22]=1)=[O:20].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[CH:1]1([N:5]2[CH2:6][CH2:7][CH:8]([CH2:11][CH:12]3[CH2:17][CH2:16][N:15]([C:24]4[CH:25]=[CH:26][C:21]([C:19](=[O:20])[CH3:18])=[CH:22][CH:23]=4)[CH2:14][CH2:13]3)[CH2:9][CH2:10]2)[CH2:4][CH2:3][CH2:2]1

참가 물질

5

반응물 3

HCID 98284'-FluoroacetophenoneHCID 11430Potassium CarbonateHCID 688867961-Cyclobutyl-4-(4-piperidinylmethyl)piperidine

생성물 1

HCID 115449041-(4-{4-[(1-Cyclobutyl-4-piperidinyl)methyl]-1-piperidinyl}phenyl)ethanone수율 22.2%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
120 °C

실험 절차

1-Cyclobutyl-4-(4-piperidinylmethyl)piperidine (may be prepared as described in Description 6) (0.15 g), 4-fluoroacetophenone (0.133 g) and potassium carbonate (0.177 g) were dissolved in DMSO (2 ml) and heated at 120° C. for 7 min in the microwave reactor. The crude reaction mixture was passed through an SCX column (10 g, eluting with methanol [80 ml] then 2 N NH3 in methanol [80 ml]). Chromatography of the crude ketone (silica gel, eluting with methanol/dichloromethane, 0-25%) afforded the title compound (E25) (0.05 g). MS electrospray (+ion) 355 (MH+).

후처리

  1. customThe crude reaction mixture
  2. washeluting with methanol [80 ml]

출처 및 근거

ORD 기록
ord-2dc4eaaad3bc4d16b4b9fdb9c76216c5
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07638631B2

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