2-(Dimethylamino)ethanol → 6-(2-Dimethylaminoethoxy)-1-tetralone

HRID 32046

Reaktionsgleichung

Reaktionsgleichung von HRID 32046
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2.[CH3:13][N:14]([CH3:18])[CH2:15][CH2:16]O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>CCOCC>[CH3:13][N:14]([CH3:18])[CH2:15][CH2:16][O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2

Komponenten

6

Edukt 4

HCID 79022-(Dimethylamino)ethanolHCID 11776TriphenylphosphineHCID 46794946-Hydroxy-3,4-dihydro-1(2H)-naphthalenoneHCID 5462977Diethyl azodicarboxylate

Produkt 1

HCID 122143876-(2-Dimethylaminoethoxy)-1-tetralone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

Ether linked analogs such as 45, are prepared by the convergent synthesis depicted in scheme 13. The 6-hydroxy-1-tetralone 14 is reacted with an amine, such as N,N-dimethylethanolamine, preferably in the presence of PPh3 and DEAD at a temperature preferably between about 0° C. and about RT to form the 6-(2-dimethylamino-ethoxy)-3,4-dihydro-2H-naphthalen-1-one 42. the 6-(2-dimethylamino-ethoxy)-3,4-dihydro-2H-naphthalen-1-one 42 is reacted with hydroxylamine hydrochloride and base, such as Et3N. The reaction is heated above RT, preferably at reflux to form the oxime 43. Hydrogenation of the oxime 43, such as with Pd/C and H2 provides the amine 44 which can be coupled with the appropriate acid to form the desired compound 45.

Quellen und Nachweise

ORD-Eintrag
ord-fb518a5ff6cf444a9f48de5370aa9347
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425631B2

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