[Cl:1][CH:2](Cl)[C:3](=[O:22])[C:4]([NH:8][C:9](=[O:21])[C:10]1[CH:15]=[CH:14][C:13]([N:16]([CH2:19][CH3:20])[CH2:17][CH3:18])=[CH:12][CH:11]=1)([CH2:6][CH3:7])[CH3:5].C(O)C.C.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.[Pd]>[Cl:1][CH2:2][C:3](=[O:22])[C:4]([NH:8][C:9](=[O:21])[C:10]1[CH:11]=[CH:12][C:13]([N:16]([CH2:17][CH3:18])[CH2:19][CH3:20])=[CH:14][CH:15]=1)([CH2:6][CH3:7])[CH3:5]
The N-(3,3-dichloro-1-ethyl-1-methyl-2-oxopropyl)-4-diethylaminobenzamide (390 mg) prepared in the previous step, 50 mL of ethanol and 75 mg of 5% palladium over charcoal were placed in a hydrogenation bottle and hydrogenated in a Parr apparatus (50 psia, room temperature) for 3 hours. The reaction mixture was filtered through celite and the solvent eliminated under reduced pressure, to yield a crude product. The crude product was dissolved in ethyl acetate and then shaken with saturated aqueous sodium bicarbonate. The phases were separated and the organic layer was dried over anhydrous magnesium sulfate. The solvent was then eliminated using a rotary evaporator, yielding 270 mg N-(3-chloro-1-ethyl-1-methyl-2-oxopropyl)-4-diethylamino-benzamide.
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