Acetic Acid → HCID 53819161, compound

Participants

Reaction Steps

1 Benzyl-4-[N-methyl-N-(2-nitro-4-fluorophenyl)amino]piperidine (EXAMPLE 169, 3.0, 8.73 mmol) and platinum oxide (1.5 g) in 100 ml ethanol is hydrogenated under 69 kPa (10 psi) hydrogen for one hr. Filtration and evaporation of the solvent gives a product which is dissolved in methanol (0.2M) and cooled to 0°. Acetone (0.71 ml, 9.60 mmol) and acetic acid (5.0 ml, 87.3 mmol) is added. After 10 minutes of stirring, sodium cyanoborohydride (628 mg, 9.25 mmol) is added and the mixture warmed to 20°-25°. Twice more the mixture is cooled to 0° and acetone (9.60 mmol) and sodium cyanoborohydride (9.25 mmol) are added, warming to 20°-25° each time. The mixture is diluted with sodium hydroxide (1N) and extracted with chloroform. The extract is dried over sodium sulfate, filtered, and evaporated to give the tide compound, NMR (300 MHz, CD3OD) 7.29, 7.0, 6.30, 6.22, 3.55, 3.47, 2.95, 2.70, 2.50, 2.0, 1.50 and 1.18δ.

Provenance & Evidence