1-(2,4-Dichlorobenzyl)piperazine → 1-{2-[4-(2,4-Dichlorobenzyl)piperazin-1-yl]-2-oxoethyl}-3-phenylpiperidin-2-one

HRID 1667180Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1667180
[O:1]=[C:2]1[CH:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][N:3]1[CH2:14][C:15]([OH:17])=O.[Cl:18][C:19]1[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:20]=1[CH2:21][N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.Cl.C(N=C=NCCCN(C)C)C>ClCCl>[Cl:18][C:19]1[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:20]=1[CH2:21][N:22]1[CH2:23][CH2:24][N:25]([C:15](=[O:17])[CH2:14][N:3]2[CH2:4][CH2:5][CH2:6][CH:7]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:2]2=[O:1])[CH2:26][CH2:27]1

Komponenten

5

Edukt 3

HCID 4111791-(2,4-Dichlorobenzyl)piperazineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 673587022-(2-Oxo-3-phenylpiperidin-1-yl)acetic acid

Produkt 1

HCID 452754981-{2-[4-(2,4-Dichlorobenzyl)piperazin-1-yl]-2-oxoethyl}-3-phenylpiperidin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 2-(2-oxo-3-phenylpiperidin-1-yl)acetic acid (Example 91D, 0.050 g, 0.214 mmol), 1-(2,4-dichlorobenzyl)piperazine (0.058 g, 0.236 mmol) and N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (0.062 g, 0.322 mmol) in dichloromethane (0.5 mL) was allowed to stir at ambient temperature. After stirring overnight, the reaction was loaded directly onto a SF10-8 silica gel column (Analogix®, Burlington, Wis.), and the title compound was eluted using a gradient of 5% to 100% ethyl acetate/hexanes over 20 minutes, maintaining 100% ethyl acetate for an additional 5 minutes (flow=20 mL/minute). 1H NMR (300 MHz, CDCl3) δ ppm 7.36-7.42 (m, 2H), 7.17-7.34 (m, 6H), 4.45 (d, J=15.5 Hz, 1H), 4.05 (d, J=15.5 Hz, 1H), 3.71 (dd, J=7.7, 6.0 Hz, 1H), 3.64 (t, J=4.9 Hz, 2H), 3.58 (s, 2H), 3.53-3.61 (m, 1H), 3.46-3.51 (m, 2H), 3.39-3.48 (m, 1H), 2.48-2.52 (m, 4H), 2.17-2.27 (m, 1H), 1.95-2.08 (m, 2H), 1.80-1.91 (m, 1H); MS (ESI+) m/z 460 (M+H)+.

Aufarbeitung

  1. stirringAfter stirring overnight
  2. washthe title compound was eluted
  3. customover 20 minutes
  4. temperaturemaintaining 100% ethyl acetate for an additional 5 minutes (flow=20 mL/minute)

Quellen und Nachweise

ORD-Eintrag
ord-19eb77fd495d4394996c99ba0fe5c48f
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08044069B2

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