Ethyl 1-(phenylmethyl)-4-piperidinecarboxylate

Colourless Oil

2f) Ethyl 4-benzylisonipecotateA mixture of ethyl isonipecotate (65 mmol; 10.2 g), anhydrous potassium carbonate (195 mmol; 26.9 g) and benzyl bromide (78 mmol; 13.36 g) in anhydrous Λ/, Λ/-dimethylformamide (100 ml) was stirred at 70Ethyl isonipecotate (1, 50 g, 0.31 mol) was dissolved in toluene (150 mL) in a round bottom flask, charged with potassium carbonate (60 g, 0.43 mol) and stirred for 15 min. Benzyl chloride (42 g, 0.31 mol) was charged and the reaction mass was refluxed for 4 h at 100 °C. Upon completion of the reaction as marked by TLC (hexane:ethyl acetate; 2:1), the reaction mass was cooled to room temperature and quenched with water (100 mL), stirred and the organic phase was separated. The aqueous phase was again extracted with toluene (100 mL). Combined organic phase was washed twice with saturated brine solution (50 mL). Remove toluene in vacuo to obtain N-benzyl ethyl isonipecotate (2, 6.97 g, 91 percent) as a yellow liquid.(a) The 18.4g4- isonipecotate hydrochloride, 12.7g of benzyl chloride, 21.0 g of sodium bicarbonate and 40ml of absolute ethanol was added to a 100ml reaction flask, was heated to reflux and maintained at reflux the reaction 3h, cooled to an internal temperature 30 about, filtering, washing the filter cake with 20ml ethanol, and the filtrate was concentrated to a paste, added 40ml of toluene and 40ml of water, stirred and dispersed organic layer was separated, the toluene was concentrated to give 1-benzyl-4-piperidinecarboxylic acid ethyl ester 23.2g, as a pale yellow oily liquid. Yield: 93.8percent (in terms benzyl chloride). HPLC: 98.74percent

Molecular Weight:247.33
XLogP3:2.5
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:5
Exact Mass:247.157228913
Monoisotopic Mass:247.157228913
Topological Polar Surface Area:29.5
Heavy Atom Count:18
Complexity:253
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes