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

HRID 1436870노트

반응식

HRID 1436870 반응식
[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]

참가 물질

6

반응물 2

HCID 690609141-(4-Fluorobenzyl)-4-(1-methyl-1-nitroethyl)piperidin-2-oneHCID 178418361HCID 178418361, 화합물

생성물 1

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

시약·촉매·용매 3

HCID 935Nickel촉매HCID 702Ethanol용매HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e3a1fcdcfd5a4bde82e9fe2cbdd552d8
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07619086B2

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