Aluminium lithium hydride → alpha-methyl-N,N-diethyl-1-phenyl-2,5-cyclohexadien-1-ethylamine
Reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:9]([CH:13]([CH3:27])[CH2:14][C:15]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:20]=[CH:19][CH2:18][CH:17]=[CH:16]1)[C:10](=O)[CH3:11])[CH3:8]>O1CCCC1>[CH3:27][CH:13]([N:9]([CH2:10][CH3:11])[CH2:7][CH3:8])[CH2:14][C:15]1([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:16]=[CH:17][CH2:18][CH:19]=[CH:20]1Participants
4
Procedure
0.266 g. of lithium aluminum hydride is placed in 10 ml. of tetrahydrofuran. After the addition of 1 g. of N-ethyl-N-[1-methyl-2-(1-phenyl-2,5-cyclohexadien-1-yl)ethyl]-acetamide in 10 ml. of tetrahydrofuan, the mixture is stirred at room temperature for 7 hours. Subsequently, excess lithium aluminum hydride is destroyed by the addition of ethyl aceate and of water. The mixture is filtered and the filter is rinsed with ether. After separation of the phases, the organic phase is dried with sodium sulfate, filtered and concentrated completely. The crude product is chromatographed on 60 g. of Alox neutral with ethyl acetate. There is obtained α-methyl-N,N-diethyl-1-phenyl-2,5-cyclohexadien-1-ethylamine in the form of an oily product. This is converted as usual into the hydrochloride which, after crystallization from methylene chloride/ether, has a melting point of 172°-174° C.