Diisopropylethylamine → HCID 178482921, compound

Participants

Reaction Steps

A suspension of trans-4-(4-nitro-3-trifluoromethyl-phenylamino)-cyclohexanecarboxylic acid (7.88 g; 23.7 mmol, prepared in accordance with Example 42), diisopropylethyl amine (8.56 mL; 47.4 mmol), and tetramethyl-O-(1H-benzotriazol-1-yl)uronium hexafluorophosphate (8.74 g; 22.6 mmol) in a mixture of dichloromethane (300 mL) and dimethylsulfoxide (5 mL) was stirred for 20 min. Afterward, methyl-[1-(4-trifluoromethyl-phenyl)-piperidin-4-ylmethyl]-amine (6.15 g; 22.6 mmol, prepared in accordance with Example 56) was added. The resulting suspension was stirred for 15.5 hr at room temperature. This resulted in a clear solution, which was extracted with water (1 L). The organic phase was dried over sodium sulfate. After concentrating under reduced pressure, the resulting residue obtained was dissolved in a small volume of acetonitrile and filtered over a silica gel pad. The solvent was removed under reduced pressure, and the resulting solid was dried at 40° C. under a pressure of 3 mbar to afford the desired product (12.9; 22.0 mmol).

Provenance & Evidence