Phenylsilane → N-(2-((4-chlorophenethyl)(piperidin-4-yl)amino)ethyl)benzamide

HRID 59788

Reaktionsgleichung

Reaktionsgleichung von HRID 59788
[C:1]([NH:9][CH2:10][CH2:11][N:12]([CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=1)[CH:13]1[CH2:18][CH2:17][N:16](C(OCC=C)=O)[CH2:15][CH2:14]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1([SiH3])C=CC=CC=1>C(Cl)Cl>[Cl:33][C:30]1[CH:29]=[CH:28][C:27]([CH2:26][CH2:25][N:12]([CH:13]2[CH2:14][CH2:15][NH:16][CH2:17][CH2:18]2)[CH2:11][CH2:10][NH:9][C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:32][CH:31]=1

Komponenten

4

Edukt 2

HCID 12752PhenylsilaneHCID 121410296Allyl 4-((2-benzamidoethyl)(4-chlorophenethyl)amino)piperidine-1-carboxylate

Produkt 1

HCID 121410331N-(2-((4-chlorophenethyl)(piperidin-4-yl)amino)ethyl)benzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The solution of allyl 4-((2-benzamidoethyl)(4-chlorophenethyl)amino)piperidine-1-carboxylate, PhSiH3 (5 equiv) in DCM (8 mL/mmol) was degassed for 10 min by bubbling argon through the inserted needle, prior to the addition of Pd(Ph3P)4 (5 mol %). After 20 min TLC indicated completion of reaction. The reaction was concentrated and was purified by column chromatography in DCM/MeOH solvent system (gradient 100:1 to 10:1) to give pure product in a form of an off-white solid.

Aufarbeitung

  1. customby bubbling argon through the inserted needle
  2. additionto the addition of Pd(Ph3P)4 (5 mol %)
  3. customAfter 20 min TLC indicated completion of reaction
  4. concentrationThe reaction was concentrated
  5. customwas purified by column chromatography in DCM/MeOH solvent system (gradient 100:1 to 10:1)
  6. customto give pure product in a form of an off-white solid

Quellen und Nachweise

ORD-Eintrag
ord-15eac85c8f2845f999467b18e820542b
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440953B2

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