Methyl vinyl sulfone → 1-[3-(Ethyloxy)-4-nitrophenyl]-4-{1-[2-(methylsulfonyl)ethyl]-4-piperidinyl}-piperazine

HRID 419401노트

반응식

HRID 419401 반응식
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([N:13]2[CH2:18][CH2:17][N:16]([CH:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[CH2:15][CH2:14]2)[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[CH3:2].[CH:25]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH2:26]>O1CCOCC1>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([N:13]2[CH2:14][CH2:15][N:16]([CH:19]3[CH2:24][CH2:23][N:22]([CH2:26][CH2:25][S:27]([CH3:30])(=[O:29])=[O:28])[CH2:21][CH2:20]3)[CH2:17][CH2:18]2)[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[CH3:2]

참가 물질

4

반응물 2

HCID 19354Methyl vinyl sulfoneHCID 594528881-[3-(Ethyloxy)-4-nitrophenyl]-4-(4-piperidinyl)piperazine

생성물 1

HCID 666496531-[3-(Ethyloxy)-4-nitrophenyl]-4-{1-[2-(methylsulfonyl)ethyl]-4-piperidinyl}-piperazine수율 74%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

반응 조건

온도
95 °C

실험 절차

A mixture of 1-[3-(ethyloxy)-4-nitrophenyl]-4-(4-piperidinyl)piperazine (Example 91, step A) (0.30 g, 0.90 mmol) and methyl vinyl sulfone (0.29 g, 2.7 mmol) in dioxane (9.0 mL) was stirred under N2. The reaction was heated to 95° C. and stirred for approximately 3 h, then cooled to rt. The reaction mixture was concentrated under vacuum. The residue was taken up in DCM and aqueous (saturated) NaHCO3. The aqueous layer was extracted with DCM (3×). The combined organic layers were dried over MgSO4 and concentrated under vacuum. The residue was chromatographed on silica gel to give the title compound of step A (294 mg, 0.66 mmol, 74%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 7.85 (d, 1H, J=9.35 Hz), 6.56 (dd, 1H, J=9.44 and 2.29 Hz), 6.49 (d, 1H, J=2.38 Hz), 4.17 (q, 2H, J=6.96 Hz), 3.36-3.41 (m, 4H), 3.25 (t, 2H, J=6.78 Hz), 3.01 (s, 3H), 2.92 (M, 2H), 2.66 (t, 2H, J=6.78 Hz), 2.57 (m, 4H), 2.15-2.25 (m, 1H), 1.89-1.97 (m, 2H), 1.75 (m, 2H), 1.32-1.40 (m, 5H).

후처리

  1. stirringstirred for approximately 3 h
  2. temperaturecooled to rt
  3. concentrationThe reaction mixture was concentrated under vacuum
  4. extractionThe aqueous layer was extracted with DCM (3×)
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. concentrationconcentrated under vacuum
  7. customThe residue was chromatographed on silica gel

출처 및 근거

ORD 기록
ord-f7cec228d4dc451893c59d7398f5311d
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093239B2

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