tert-Butyl 4-(2-methoxybenzylamino)piperidine-1-carboxylate synthesis

Yield:359877-80-8 211 mg

Reaction Conditions:

with sodium cyanoborohydride;acetic acid in methanol at 20; for 24 h;

Steps:

22

Example 22
N-((2-Methoxyphenyl)methyl)-N-(piperidin-4-yl)-4-methoxyphenylmethylacetamide (26HCH80-4)
To a solution of commercially available tert-butyl 4-oxo-1-piperidine carboxylate (400 mg, 2 mmol) in methanol (1 ml) and 2-methoxybenzylamine (0.130 ml, 1 mmol) in methanol (1 ml) was added acetic acid in methanol (1 M, 1.34 ml) followed by NaCNBH₃ in methanol (0.3 M, 4.4 ml).
The resulting solution was stirred at room temperature.
After 24 h, water (2 ml) was added, and the mixture was stirred for 1 h, before it was concentrated.
The resulting oil was redissolved in diethyl ether (20 ml), extracted with HCl (0.1 N, 1*15 ml).
The aqueous layer was washed with diethyl ether (10 ml) and treated with 0.2 N NaOH until basic (pH>8), before extracted with dichloromethane (20 ml).
The organic layer was dried (Na₂SO₄), filtered, and concentrated to give tert-butyl 4-((2-methoxyphenyl)methyl)amino-piperidine carboxylate. Yield: 211 mg.

References:

US2015/259291,2015,A1 Location in patent:Paragraph 0310