2-(4-Chloro-2-nitro-phenoxy)-1-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-ethanone → 2-(2-amino-4-chloro-phenoxy)-1-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-ethanone

HRID 480187

Reaction equation

HRID 480187 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([O:6][CH2:7][C:8]([N:10]2[CH2:15][C@H:14]([CH3:16])[N:13]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[CH2:12][C@H:11]2[CH3:25])=[O:9])=[C:4]([N+:28]([O-])=O)[CH:3]=1.[H][H]>C(O)C.[Pt]>[NH2:28][C:4]1[CH:3]=[C:2]([Cl:1])[CH:27]=[CH:26][C:5]=1[O:6][CH2:7][C:8]([N:10]1[CH2:15][C@H:14]([CH3:16])[N:13]([CH2:17][C:18]2[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=2)[CH2:12][C@H:11]1[CH3:25])=[O:9]

Participants

5

Reactant 2

HCID 444315252-(4-Chloro-2-nitro-phenoxy)-1-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-ethanoneHCID 178418361HCID 178418361, compound

Product 1

HCID 540805932-(2-amino-4-chloro-phenoxy)-1-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-ethanoneYield 70%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

To a solution of (2R, 5S)-2-(4-chloro-2-nitro-phenoxy)-1-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-ethanone (2.2 g, 5.05 mmol) in ethanol (50 ml) in a par bottle was added 5% platinum on carbon (2.2 g). The reaction mixture was subjected to hydrogen gas (35 psi) for thirty minutes. The reaction mixture was filtered through celite and washed with ethanol. The filtrate was concentrated to give a tan foam. Chromatography on silica gel gave the title compound (1.42 g, 70% yield).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washwashed with ethanol
  3. concentrationThe filtrate was concentrated
  4. customto give a tan foam

Sources & evidence

ORD record
ord-a00bcc4e521f4c878ab46a4dd9ae779f
Source dataset
uspto-grants-2003_11
Patent number
US06649611B2

Linked notes

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