1,2-Dichloroethane → HCID 67130576, Verbindung
Reaktionsgleichung
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1.Cl[C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH:26]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.[Cl:49]CCCl>>[Cl:49][C:30]1[CH:29]=[CH:28][C:25]([CH2:26][NH:1][C:2]2[CH:3]=[CH:4][C:5]([C:8]([N:10]3[CH2:15][CH2:14][N:13]([C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH2:12][CH2:11]3)=[O:9])=[CH:6][CH:7]=2)=[CH:24][CH:23]=1Komponenten
Versuchsvorschrift
To a stirred solution of (4-amino-phenyl)-(4-phenyl-piperazin-1-yl)-methanone (200 mg, 0.71 mmol) in 1,2-dichloroethane (4 ml) at 0° C. was added 3-chlorobenzaldehyde (99.7 mg, 0.71 mmol). Sodium triacetoxy borohydride (210 mg, 0.99 mmol) and acetic acid (40.6 μl, 0.71 mmol) were added and the reaction was stirred at room temperature under nitrogen overnight. The reaction was quenched with the addition of sodium hydroxide (aq.) (pH8) and extracted with diethyl ether (3×20 ml). The organic extracts were combined, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by flash chromatography to afford the title compound as a yellow solid (72 mg, 25% yield). HPLC retention time 7.5 min. Mass spectrum (ES+) m/z 406 (M+H).
Aufarbeitung
- customThe reaction was quenched with the addition of sodium hydroxide (aq.) (pH8)
- extractionextracted with diethyl ether (3×20 ml)
- dry with materialdried over magnesium sulfate
- concentrationconcentrated in vacuo
- customThe residue was purified by flash chromatography
Quellen und Nachweise
- ORD-Eintrag
- ord-179fa51d375149e885fef553c0829395
- Quelldatensatz
- uspto-grants-2012_09
- Patentnummer
- US08258138B2
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