Nitromethane → 1-(4-Fluorobenzyl)-4-(nitromethyl)piperidin-2-one

HRID 1436867Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1436867
[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]([CH3:19])([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]([CH2:19][N+:16]([O-:18])=[O:17])[CH2:9][C:8]2=[O:13])=[CH:14][CH:15]=1

Komponenten

4

Edukt 3

HCID 6375NitromethaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 690647451-(4-Fluorobenzyl)-5,6-dihydropyridin-2-(1H)-one

Produkt 1

HCID 690699721-(4-Fluorobenzyl)-4-(nitromethyl)piperidin-2-one

Versuchsvorschrift

To a solution of 1-(4-fluorobenzyl)-5,6-dihydropyridin-2-(1H)-one (6.2 g, 30 mmol) in nitromethane (64.5 g, 1.06 mol) under an atmosphere of nitrogen was added DBU (4.59 g, 30.2 mmol). The reaction mixture was stirred overnight at room temperature. The product mixture was concentrated under vacuum. The residue was purified using column chromatography on silica gel eluting with 50%-100% ethyl acetate in hexanes. Collection and concentration of appropriate fractions provided the title compound as pale yellow oil. 1H NMR (400 MHz, CDCl3) δ 7.25 (m, 2H), 7.01 (t, J=8.7 Hz, 2H), 4.64 (d, J=14.6 Hz, 1H), 4.48 (d, J=14.5 Hz, 1H), 4.34 (m, 2H), 3.27 (m, 2H), 2.23 (dd, J=17, 10.6 Hz, 1H), 2.0 (m, 1H), 1.61 (m, 1H).

Aufarbeitung

  1. concentrationThe product mixture was concentrated under vacuum
  2. customThe residue was purified
  3. customCollection and concentration of appropriate fractions

Quellen und Nachweise

ORD-Eintrag
ord-3f6921c30afc4616b0b754fb78c277a4
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07619086B2

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