1-(4-Fluorobenzyl)-4-(1-methyl-1-nitroethyl)piperidin-2-one → 4-(1-Amino-1-methylethyl)-1-(4-fluorobenzyl)piperidine-2-one

HRID 1436870ノート

反応式

HRID 1436870 の反応式
[F:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][CH:10]([C:13]([CH3:18])([N+:15]([O-])=O)[CH3:14])[CH2:9][C:8]2=[O:19])=[CH:4][CH:3]=1.[H][H]>C(O)C.[Ni].O>[NH2:15][C:13]([CH:10]1[CH2:11][CH2:12][N:7]([CH2:6][C:5]2[CH:20]=[CH:21][C:2]([F:1])=[CH:3][CH:4]=2)[C:8](=[O:19])[CH2:9]1)([CH3:18])[CH3:14]

参加物

6

反応物 2

HCID 690609141-(4-Fluorobenzyl)-4-(1-methyl-1-nitroethyl)piperidin-2-oneHCID 178418361HCID 178418361、化合物

生成物 1

HCID 690668314-(1-Amino-1-methylethyl)-1-(4-fluorobenzyl)piperidine-2-one

試薬・触媒・溶媒 3

HCID 935Nickel触媒HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

To a solution of 1-(4-fluorobenzyl)-4-(1-methyl-1-nitroethyl)piperidin-2-one (1.05 g, 3.57 mmol) in degassed ethanol (75 mL) was added Raney Nickel (2 g of a 50% by weight slurry in water). The reaction mixture was shaken under 55 psi of hydrogen fro 4 hours. The reaction mixture was filtered through a bed a celite, then concentrated under vacuum to give an oil that solidified on standing. The solid was triturated in ether and collected by filtration to give the title compound. 1H NMR (400 MHz, CDCl3) δ 7.22 (m, 2H), 7.02 (t, J=8.6 Hz, 2H), 4.65 (d, J=14.5 Hz, 1H), 4.44 (d, J=14.6 Hz, 1H), 3.26 (m, 2H), 2.60 (d, J=5 Hz, 1H), 2.25 (m, 1H), 1.97 (d, J=11.5 Hz, 1H), 1.75 (m, 1H), 1.44 (m, 1H), 1.11 (d, J=9 Hz, 6H) ppm. ES MS M+1=265.

後処理

  1. filtrationThe reaction mixture was filtered through a bed a celite
  2. concentrationconcentrated under vacuum
  3. customto give an oil that
  4. customThe solid was triturated in ether
  5. filtrationcollected by filtration

出典と根拠

ORDレコード
ord-e3a1fcdcfd5a4bde82e9fe2cbdd552d8
出典データセット
uspto-grants-2009_11
特許番号
US07619086B2

反応ノート

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