[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]/[CH:9]=[CH:10]/[CH2:11][N:12]([CH2:15][CH3:16])[CH2:13][CH3:14])=[CH:4][CH:3]=1.C.[H][H]>C(O)(=O)C.[Pt]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][N:12]([CH2:15][CH3:16])[CH2:13][CH3:14])=[CH:6][CH:7]=1Add 2.0 g (0.0084 mole) of (E)-4-(4-chlorophenyl)-N,N-diethyl-2-buten-1-amine to flask containing 0.20 g platinum (5%) on activated charcoal suspended in 15 ml glacial acetic acid. Stir reaction mixture under one atmosphere hydrogen until hydrogen absorption ceases (41/2 hours). Filter reaction mixture with methylene chloride wash and 50 ml distilled water. Separate layers and extract aqueous with 3×70 ml methylene chloride. Combine methylene chloride extracts and wash with cold 2×75 ml 1N NaOH. Dry organic layer over MgSO4, filter and evaporate to yield the title compound.
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