[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)([CH3:4])([CH3:3])[CH3:2].[C:17]([CH2:19][C:20](O)=[O:21])#[N:18].C(N(CC)CC)C.O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1>C(Cl)Cl>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][N:14]([C:20](=[O:21])[CH2:19][C:17]#[N:18])[CH2:13][CH2:12]1)([CH3:4])([CH3:2])[CH3:3]
To a stirred solution of provide 1-(2-tert-butylphenyl)piperazine (0.203 g, 0.69 mmol), 2-cyanoacetic acid (0.065 g, 0.77 mmol) and triethylamine (0.279 g, 2.76 mmol) in methylene chloride (5.0 mL) was added bis(2-oxo-3-oxazolidinyl)phosphinic chloride (0.202 g, 0.77 mmol) at room temperature. After 2.5 h the reaction mixture was diluted with methylene chloride (10.0 mL), washed with water (20.0 mL), dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel, 50% ethyl acetate/heptanes) to provide 3-(4-(2-tert-butylphenyl)piperazin-1-yl)-3-oxopropanenitrile (0.114 g, 58%) as an off-white solid, mp 163-164° C.
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