Hydrochloric Acid → 5-((S)-1,3'-bipiperidin-4-yl)-2-chloro-N-((R)-1-(2,4-dichlorophenyl)ethyl)aniline

HRID 75129Notes

Reaction equation

HRID 75129 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:16]([C:19]2[CH2:20][CH2:21][N:22]([C@H:25]3[CH2:30][CH2:29][CH2:28][NH:27][CH2:26]3)[CH2:23][CH:24]=2)=[CH:15][C:3]=1[NH:4][C@@H:5]([C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=1[Cl:14])[CH3:6].Cl>C(O)C.[Pt](=O)=O>[N:22]1([C@H:25]2[CH2:30][CH2:29][CH2:28][NH:27][CH2:26]2)[CH2:21][CH2:20][CH:19]([C:16]2[CH:17]=[CH:18][C:2]([Cl:1])=[C:3]([CH:15]=2)[NH:4][C@@H:5]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=2[Cl:14])[CH3:6])[CH2:24][CH2:23]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 866890422-chloro-N-((R)-1-(2,4-dichlorophenyl)ethyl)-5-(1-((S)-3-piperidyl)-3,6-dihydro-2H-pyridin-4-yl)aniline

Product 1

HCID 866890445-((S)-1,3'-bipiperidin-4-yl)-2-chloro-N-((R)-1-(2,4-dichlorophenyl)ethyl)aniline

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent2×

Procedure

A mixture of the crude 2-chloro-N-((1R)-1-(2,4-dichlorophenyl)ethyl)-5-(1-((3S)-3-piperidyl)-3,6-dihydro-2H-pyridin-4-yl)aniline (0.30 g, 0.63 mmol), platinum(IV) oxide (PtO2) (5% by weight, 0.045 g) in ethanol (3 mL) containing concentrated hydrochloric acid (conc. HCl) (0.20 mL, 2.20 mmol) in a Paar shaker flask was hydrogenated at 40 psi for 45 min. The reaction mixture was diluted with ethanol, and filtered through the Celite. The filtrate was concentrated in vacuo, and the resulting residue was diluted with dichloromethane (25 mL). The organic layer was washed with saturated aqueous sodium bicarbonate solution, dried (Na2SO4), filtered, and concentrated in vacuo. The residue was used without further purification (0.27 g, 0.058 mmol). MS: (ES) m/z calculated for C24H31Cl3N3 [M+H]+466.2. found 466.

Workup

  1. filtrationfiltered through the Celite
  2. concentrationThe filtrate was concentrated in vacuo
  3. additionthe resulting residue was diluted with dichloromethane (25 mL)
  4. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was used without further purification (0.27 g, 0.058 mmol)

Sources & evidence

ORD record
ord-d54dae00a2494efaa5146ff02447b23f
Source dataset
uspto-grants-2014_09
Patent number
US08835419B2

Reaction notes

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