4-Nitrobenzyl bromide → HCID 19045334, Verbindung

HRID 1781384Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1781384
[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-acetamidospiro[(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-947d6841260549d3b54d67fb4a7179a9
Quelldatensatz
uspto-grants-1997_05
Patentnummer
US05633247

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