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

HRID 75129ノート

反応式

HRID 75129 の反応式
[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

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 345198Adams' catalyst触媒HCID 702Ethanol溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-d54dae00a2494efaa5146ff02447b23f
出典データセット
uspto-grants-2014_09
特許番号
US08835419B2

反応ノート

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