Sodium hydride → HCID 18445309, compound

Participants

Reaction Steps

Add dropwise a solution of 4-benzylamino-cyclohexanol (675 mg, 3.28 mmol) in DMF (2 mL) to a suspension of NaH (196 mg, 4.92 mmol) in DMF (3 mL). Stir at room temperature for 45 min then at 50° C. for additional 40 min. Add a solution of 6-chloro-nicotinonitrile (500 mg, 3.61 mmol) in DMF (1.8 mL) dropwise and stir overnight at 60° C. Cool down the reaction mixture and evaporate the solvent. Wash the residue with water (10) and extract with EtOAc/hex (2/1, 15 mL). Combine the organic layers and dry over sodium sulfate. Filter and concentrate. Purify the resulting residue through an SCX column. Further purified by chromatography [CH2Cl2/NH3 (2.0M in methanol) 20/1] to provide the title compound (890 mg, 88%).

Provenance & Evidence