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

HRID 1269439Notes

Reaction equation

HRID 1269439 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Ether linked analogs such as 61, are prepared by the convergent synthesis depicted in scheme 15. The 6-hydroxy-1-tetralone 15 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 59. The 6-(2-dimethylamino-ethoxy)-3,4-dihydro-2H-naphthalen-1-one 59 is reacted with hydroxylamine hydrochloride and base, such as Et3N. The reaction is heated above RT, preferably at reflux to form the oxime 60. Hydrogenation of the oxime 60, such as with Pd/C and H2 provides the amine 61.

Sources & evidence

ORD record
ord-fb530ee4165240bf9a6c0ed4bbf8fcae
Source dataset
uspto-grants-2007_04
Patent number
US07199244B2

Reaction notes

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