4-Nitrobenzyl bromide → HCID 19045334, Verbindung

HRID 1591182Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1591182
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8]Br)=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:12]([NH:15][C:16]1[CH:17]=[CH:18][C:19]2[O:29][C:23]3([CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)[CH2:22][C:21](=[O:30])[C:20]=2[CH:31]=1)(=[O:14])[CH3:13].C(N(C(C)C)CC)(C)C.CO.C(Cl)(Cl)Cl>CN(C)C=O>[C:12]([NH:15][C:16]1[CH:17]=[CH:18][C:19]2[O:29][C:23]3([CH2:24][CH2:25][N:26]([CH2:8][C:7]4[CH:10]=[CH:11][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=4)[CH2:27][CH2:28]3)[CH2:22][C:21](=[O:30])[C:20]=2[CH:31]=1)(=[O:14])[CH3:13]

Komponenten

6

Edukt 4

HCID 660114-Nitrobenzyl bromideHCID 81531DiisopropylethylamineHCID 19045273HCID 19045273, VerbindungHCID 21584188Chloroform methanol

Produkt 1

HCID 19045334HCID 19045334, VerbindungAusbeute 59,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 4-nitrobenzyl bromide (0.73 g, 3.4 mmol), 3,4-dihydro-6-acetamido spiro[(2H)-benzopyran-2,4'-piperidine]-4-one (0.94 g, 3.4 mmol) and diisopropylethylamine (0.61 ml, 3.5 mmol) in dimethylformamide (15 ml) was stirred at room temperature for 3 hr. The reaction mixture was then concentrated under reduced pressure. The residue was diluted with methylene chloride and washed with saturated sodium bicarbonate solution, water and brine. Drying and solvent evaporation gave an oil; flash chromatography (silica gel, methanol-chloroform 2/98) gave 3,4-dihydro-6-acetamido-1'-(4-nitrobenzyl)spiro[(2H)-1-benzopyran-2,4'-piperidine]-4-one (0.83 g, 59%); 75 mg converted to hydrochloride; mp>250° C.

Aufarbeitung

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. additionThe residue was diluted with methylene chloride
  3. washwashed with saturated sodium bicarbonate solution, water and brine
  4. customDrying
  5. customsolvent evaporation
  6. customgave an oil

Quellen und Nachweise

ORD-Eintrag
ord-14bc5a263d1a4892bc0fcf6a64e28a43
Quelldatensatz
uspto-grants-1993_04
Patentnummer
US05206240

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