1-Piperidinecarboxamide, N-[[3,5-bis(trifluoromethyl)phenyl]methyl]-2-(4-fluoro-2-methylphenyl)-N- methyl-4-oxo-, (2R)-

Base Information

• Chemical Name: 1-Piperidinecarboxamide, N-[[3,5-bis(trifluoromethyl)phenyl]methyl]-2-(4-fluoro-2-methylphenyl)-N- methyl-4-oxo-, (2R)-
• CAS No.: 414910-14-8
• Molecular Formula: C23H21F7N2O2
• Molecular Weight: 490.421
• Mol file: 414910-14-8.mol

Synonyms:

Chemical Property of 1-Piperidinecarboxamide, N-[[3,5-bis(trifluoromethyl)phenyl]methyl]-2-(4-fluoro-2-methylphenyl)-N- methyl-4-oxo-, (2R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-Piperidinecarboxamide, N-[[3,5-bis(trifluoromethyl)phenyl]methyl]-2-(4-fluoro-2-methylphenyl)-N- methyl-4-oxo-, (2R)-

There total 9 articles about 1-Piperidinecarboxamide, N-[[3,5-bis(trifluoromethyl)phenyl]methyl]-2-(4-fluoro-2-methylphenyl)-N- methyl-4-oxo-, (2R)- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 78.0%

(2R)-2-(4-fluoro-2-methylphenyl)-4-piperidinone L-(+)-mandelate (414910-13-7) + bis(trichloromethyl) carbonate (32315-10-9) + N-[3,5-bis(trifluoromethyl)benzyl]methylamine hydrochloride → (2R)-N-{[3,5-bis(trifluoromethyl)phenyl]methyl}-2-(4-fluoro-2-methylphenyl)-N-methyl-4-oxo-1-piperidinecarboxamide (414910-14-8)

Guidance literature:

(2R)-2-(4-fluoro-2-methylphenyl)-4-piperidinone L-(+)-mandelate; With sodium hydrogencarbonate; In water; ethyl acetate; at 20 ℃; for 0.25h; Inert atmosphere;

bis(trichloromethyl) carbonate; With triethylamine; In ethyl acetate; at 0 - 20 ℃; for 3h; Inert atmosphere;

N-[3,5-bis(trifluoromethyl)benzyl]methylamine hydrochloride; With triethylamine; In ethyl acetate; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1021/jm1013264

Reference yield:

bis(trichloromethyl) carbonate (32315-10-9) + N-[3,5-bis(trifluoromethyl)benzyl]methylamine hydrochloride + (2R)-2-(4-fluoro-2-methylphenyl)-4-piperidinone (414910-12-6) → (2R)-N-{[3,5-bis(trifluoromethyl)phenyl]methyl}-2-(4-fluoro-2-methylphenyl)-N-methyl-4-oxo-1-piperidinecarboxamide (414910-14-8)

Guidance literature:

bis(trichloromethyl) carbonate; (2R)-2-(4-fluoro-2-methylphenyl)-4-piperidinone; With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 2h;

N-[3,5-bis(trifluoromethyl)benzyl]methylamine hydrochloride; In acetonitrile; at 23 ℃;

Reference yield:

phenylmethyl 2-(4-fluoro-2-methylphenyl)-4-oxo-3,4-dihydro-1(2H)-pyridinecarboxylate (414909-98-1) → (2R)-N-{[3,5-bis(trifluoromethyl)phenyl]methyl}-2-(4-fluoro-2-methylphenyl)-N-methyl-4-oxo-1-piperidinecarboxamide (414910-14-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: Wilkinson's catalyst; hydrogen / isopropyl alcohol / 5 h / 50 - 60 °C / 3750.38 Torr / Inert atmosphere; Large scale reaction

2.1: 5% Pd(II)/C(eggshell); hydrogen / isopropyl alcohol / 5 h / 20 °C / 3000.3 Torr / Inert atmosphere; Large scale reaction

2.2: Inert atmosphere; Large scale reaction

3.1: sodium hydrogencarbonate / dichloromethane; water / 0.5 h / Inert atmosphere; Large scale reaction

3.2: 20 °C / Inert atmosphere; Large scale reaction

4.1: sodium hydrogencarbonate / water; ethyl acetate / 0.25 h / 20 °C / Inert atmosphere

4.2: 3 h / 0 - 20 °C / Inert atmosphere

4.3: 2 h / 20 °C / Inert atmosphere

With Wilkinson's catalyst; 5% Pd(II)/C(eggshell); hydrogen; sodium hydrogencarbonate; In dichloromethane; water; ethyl acetate; isopropyl alcohol;

DOI:10.1021/jm1013264

upstream raw materials:

bis(trichloromethyl) carbonate

(2R)-2-(4-fluoro-2-methylphenyl)-4-piperidinone

4-methoxypyridine

phenylmethyl 2-(4-fluoro-2-methylphenyl)-4-oxo-3,4-dihydro-1(2H)-pyridinecarboxylate

Downstream raw materials:

(2R)-4-amino-1-{N-(3,5-bistrifluoromethylbenzyl)-N-methyl}aminocarbonyl-2-(4-fluoro-2-methylphenyl)piperidine

(2R,4S)-1-{N-(3,5-bistrifluoromethylbenzyl)-N-methyl}amino-carbonyl-2-(4-fluoro-2-methylphenyl)-4-hydroxypiperidine

C₂₆H₂₈F₇N₃O

C₂₇H₃₀F₇N₃O

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