Benzyl piperazine-1-carboxylate → Benzyl 4-[(2-oxo-3,3-diphenylpiperidin-1-yl)acetyl]piperazine-1-carboxylate

HRID 1667222Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1667222
[N:1]1([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[O:17]=[C:18]1[C:23]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:22][CH2:21][CH2:20][N:19]1[CH2:36][C:37](O)=[O:38].Cl.C(N=C=NCCCN(C)C)C>ClCCl>[O:17]=[C:18]1[C:23]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:22][CH2:21][CH2:20][N:19]1[CH2:36][C:37]([N:4]1[CH2:5][CH2:6][N:1]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:2][CH2:3]1)=[O:38]

Komponenten

5

Edukt 3

HCID 643495Benzyl piperazine-1-carboxylateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 673592802-(2-Oxo-3,3-diphenylpiperidin-1-yl)acetic acid

Produkt 1

HCID 67359633Benzyl 4-[(2-oxo-3,3-diphenylpiperidin-1-yl)acetyl]piperazine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of benzyl piperazine-1-carboxylate (0.196 g, 0.889 mmol), 2-(2-oxo-3,3-diphenylpiperidin-1-yl)acetic acid (0.250 g, 0.808 mmol; Example 68E) and N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (0.186 g, 0.970 mmol) were stirred together overnight in dichloromethane (5 mL). The reaction was concentrated, loaded directly onto a SF15-silica gel column (Analogix®). The product was eluted using a gradient of 5% to 100% ethyl acetate over 30 minutes to provide the title compound. 1H NMR (300 MHz, CDCl3) δ 7.46-7.07 (m, 15H), 5.15 (s, 2H), 4.22 (s, 2H), 3.75-3.30 (m, 10H), 2.73-2.53 (m, 2H), 1.85 (d, J=5.9, 2H); MS (ESI+) m/z 512.2 (M+H)+.

Aufarbeitung

  1. concentrationThe reaction was concentrated
  2. washThe product was eluted
  3. customover 30 minutes

Quellen und Nachweise

ORD-Eintrag
ord-87eb957285694b02af8d288c6326a708
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08044069B2

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