Stannous Chloride → (S)-1-(3-(2-amino-5-chlorophenoxy)piperidin-1-yl)-2,2,2-trifluoroethanone

HRID 240600Notes

Reaction equation

HRID 240600 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:21]([O-])=O)=[C:6]([CH:20]=1)[O:7][C@H:8]1[CH2:13][CH2:12][CH2:11][N:10]([C:14](=[O:19])[C:15]([F:18])([F:17])[F:16])[CH2:9]1.Cl[Sn]Cl>CCOC(C)=O.C([O-])([O-])=O.[K+].[K+]>[NH2:21][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:20][C:6]=1[O:7][C@H:8]1[CH2:13][CH2:12][CH2:11][N:10]([C:14](=[O:19])[C:15]([F:17])([F:16])[F:18])[CH2:9]1

Participants

5

Reactant 2

HCID 24479Stannous ChlorideHCID 58413019(S)-1-(3-(5-chloro-2-nitrophenoxy)piperidin-1-yl)-2,2,2-trifluoroethanone

Product 1

HCID 58413042(S)-1-(3-(2-amino-5-chlorophenoxy)piperidin-1-yl)-2,2,2-trifluoroethanone

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolvent2×HCID 11430Potassium CarbonateSolvent

Procedure

(S)-1-(3-(5-chloro-2-nitrophenoxy)piperidin-1-yl)-2,2,2-trifluoroethanone (465.0 mg) and SnCl2*H2O (1.49 g) was dissolved in EtOAc (10.0 ml) and heated at reflux for 3.5 h. The reaction mixture was diluted with EtOAc an 10% aq. K2CO3. The mixture was separated and the organic layer washed with water and brine. The organic phase was dried and poured through an hydrophobic frit. The solvent was evaporated to give the intended product.

Workup

  1. temperatureheated
  2. temperatureat reflux for 3.5 h
  3. customThe mixture was separated
  4. washthe organic layer washed with water and brine
  5. customThe organic phase was dried
  6. additionpoured through an hydrophobic frit
  7. customThe solvent was evaporated
  8. customto give the intended product

Sources & evidence

ORD record
ord-47fde4adbfcf4191b09f72551998e550
Source dataset
uspto-grants-2014_02
Patent number
US08648068B2

Reaction notes

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