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

HRID 1436867Notes

Reaction equation

HRID 1436867 reaction equation
[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

Participants

4

Reactant 3

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

Product 1

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

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-3f6921c30afc4616b0b754fb78c277a4
Source dataset
uspto-grants-2009_11
Patent number
US07619086B2

Reaction notes

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