Thionyl Chloride → Benzamide

HRID 379609

Reaktionsgleichung

Reaktionsgleichung von HRID 379609
[Si](OC1C=C(C=CC=1)C([C:14]1[CH:26]=[CH:25][C:17]([C:18]([N:20](CC)CC)=[O:19])=[CH:16][CH:15]=1)O)(C(C)(C)C)(C)C.S(Cl)(Cl)=O.C[C@H]1CN[C@H](C)CN1.O.[F-].C([N+](CC)(CC)CC)C>>[C:18]([NH2:20])(=[O:19])[C:17]1[CH:25]=[CH:26][CH:14]=[CH:15][CH:16]=1

Komponenten

5

Edukt 4

HCID 24386Thionyl ChlorideHCID 2206722,5-Dimethylpiperazine, trans-HCID 16211652Tetraethylammonium fluoride hydrateHCID 223500144-((3-((Tert-butyldimethylsilyl)oxy)phenyl)(hydroxy)methyl)-N,N-diethylbenzamide

Produkt 1

HCID 2331Benzamide

Versuchsvorschrift

4-(3-(tert-Butyldimethylsilyloxy)-α-hydroxybenzyl)-N,N-diethylbenzamide (Example 1, infra) was treated with thionyl chloride and trans-2,5-dimethylpiperazine as described in Example 5. The crude mixture of diastereomers was purified by chromatography on silica gel (Waters Prep 500) with dichloromethane:ethanol:triethylamine (100:0.25:0.1). The less mobile isomer (1.28 g, 2.5 mmol) was dissolved in acetonitrile and treated with tetraethylammonium fluoride hydrate (0.6 g, 4.0 mmol) as in Example 7 to give 0.46 g of (±)-N,N-diethyl-4-((αR*)-3-hydroxy-α-((2R*, 5S*)-2,5-dimethyl-1-piperazinyl)benzyl)benzamide as a white solid, mp 175-177° C.

Aufarbeitung

  1. additionThe crude mixture of diastereomers
  2. customwas purified by chromatography on silica gel (Waters Prep 500) with dichloromethane:ethanol:triethylamine (100:0.25:0.1)
  3. dissolutionThe less mobile isomer (1.28 g, 2.5 mmol) was dissolved in acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-e00d84cdcfe6456ca6342548a2d6eb36
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06300332B1

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