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

HRID 1436869Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1436869
[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

Komponenten

4

Edukt 3

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

Produkt 1

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

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-a9c671114a434efc93b4995a40acbdbb
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07619086B2

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