Sodium Hydroxide → 3-(3-Aminopropyl)-1-phenyl-8-(1-phenylcycloheptyl)-1,3,8-triazaspiro[4.5]decan-4-one

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Reaction Steps

This was prepared according to the procedure of A. Petric et al. (Bioorg. Med. Chem. Lett. 1998, 8, 1455). To a stirred solution of 1-phenyl-8-(1-phenylcycloheptyl)-1,3,8-triazaspiro[4.5]decan-4-one (54.3 mg, 0.135 mmol) in toluene (0.3 ml) was added a solution of NaOH (23.8 mg, 0.595 mmol) in water (0.5 ml), n-Bu4NHSO4 (70.8 mg, 0.209 mmol), and a solution of N-(t-butoxycarbonyl)-3-bromopropylamine (65.3 mg, 0.274 mmol, this was reported by B. H. Lee et al. J. Org. Chem. 1983, 48, 24) in toluene (0.7 ml) at room temperature. The reaction mixture was stirred at room temperature for 18 h, then at 90° C. for 2 h. The reaction mixture was cooled down to room temperature, diluted with water, and extracted with CH2Cl2. The extracts combined were washed with brine, dried (Na2SO4), filtered, and concentrated. The residue was purified by preparative TLC (1 mm plate×2, CH2Cl2/MeOH:95/5, two times developed) to afford 54.2 mg (71.8%) of colorless solid.

Provenance & Evidence