[S:1]1[CH:5]=[CH:4][C:3]([CH:6]2[NH:11][CH2:10][CH2:9][N:8]([C:12](OCC)=O)[CH2:7]2)=[CH:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[CH3:12][N:8]1[CH2:9][CH2:10][NH:11][CH:6]([C:3]2[CH:4]=[CH:5][S:1][CH:2]=2)[CH2:7]1A solution of 1.20 g of 3-(3-thienyl)-1-piperazine carboxylic acid, ethyl ester in 100 ml of ether was added to a suspension of 380 mg of lithium aluminum hydride in 50 ml of ether. The mixture was refluxed for 12 hours and the product recovered, giving 850 mg of 4-methyl-2-(3-thienyl)piperazine.
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