2-Nitropropane → 1-(4-Fluorobenzyl)-4-(1-methyl-1-nitroethyl)piperidin-2-one

HRID 1436869노트

반응식

HRID 1436869 반응식
[F:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][CH:10]=[CH:9][C:8]2=[O:13])=[CH:4][CH:3]=1.[N+:16]([CH:19]([CH3:21])[CH3:20])([O-:18])=[O:17].C1CCN2C(=NCCC2)CC1>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][CH:10]([C:19]([CH3:21])([N+:16]([O-:18])=[O:17])[CH3:20])[CH2:9][C:8]2=[O:13])=[CH:14][CH:15]=1

참가 물질

4

반응물 3

HCID 3982-NitropropaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 690647451-(4-Fluorobenzyl)-5,6-dihydropyridin-2-(1H)-one

생성물 1

HCID 690609141-(4-Fluorobenzyl)-4-(1-methyl-1-nitroethyl)piperidin-2-one

실험 절차

To a solution 1-(4-fluorobenzyl)-5,6-dihydropyridin-2(1H)-one (see Step 3 of Example 1) (0.75 g, 3.65 mmol) in 2-nitropropane (9.77 g, 109 mmol) was added DBU (0.56 g, 3.65 mmol). After stirring for 48 hours, the reaction mixture was concentrated under vacuum. The residual material was purified using silica gel column chromatography eluting with CH2Cl2. The appropriate fractions were combined and concentrated to afford the title compound. 1H NMR (400 MHz, CDCl3) δ 7.44 (m, 2H), 7.04 (t, J=9 Hz, 2H), 4.64 (d, J=15 Hz, 1H), 4.43 (d, J=15 Hz, 1H), 3.23 (m, 2H), 2.56 (m, 2H), 2.22 (m, 1H), 1.73 (m, 1H), 1.56 (s, 6H), 1.51 (m, 1H) ppm. ES MS M+1=295.

후처리

  1. concentrationthe reaction mixture was concentrated under vacuum
  2. customThe residual material was purified
  3. washeluting with CH2Cl2
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-a9c671114a434efc93b4995a40acbdbb
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07619086B2

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