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 11633

Reaction equation

HRID 11633 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 69.3%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-(4-chloro-2-nitro-phenoxy)-1-[4-(4-fluoro-benzyl)-(2R,5S)-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 30 minutes. The reaction mixture was filtered through celite and the filter cake was washed with ethanol. The filtrate was concentrated in vacuo. Chromatography on silica gel gave the title compound (1.42 g).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washthe filter cake was washed with ethanol
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-b2050dd585794dadb81d98c2170cc5a9
Source dataset
uspto-grants-2006_08
Patent number
US07098212B2

Linked notes

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