ChemicalBook CAS DataBase List piperidin-4-yl [1,1'-biphenyl]-2-ylcarbamate

piperidin-4-yl [1,1'-biphenyl]-2-ylcarbamate synthesis

6synthesis methods

Product Name:piperidin-4-yl [1,1'-biphenyl]-2-ylcarbamate
CAS Number:171722-92-2
Molecular formula:C18H20N2O2
Molecular Weight:296.36

171723-80-1 Synthesis

1-benzylpiperidin-4-yl [1,1'-biphenyl]-2-ylcarbamate

171723-80-1
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piperidin-4-yl [1,1'-biphenyl]-2-ylcarbamate

171722-92-2
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$52.00/250mg

Yield:171722-92-2 100%

Reaction Conditions:

Stage #1: 1-benzyl-4-piperidylbiphenyl-2-ylcarbamatewith hydrogenchloride;ethanol;water at 50; for 0.333333 h;
Stage #2: with ammonium formate;palladium on activated carbon in ethanol;water at 40; for 12 h;
Stage #3: with sodium hydroxide in water; pH=12;

Steps:

3 Biphenyl-2-ylcarbamic Acid Piperidin-4-yl Ester

Preparation 3 Biphenyl-2-ylcarbamic Acid Piperidin-4-yl Ester Biphenyl-2-isocyanate (97.5 g, 521 mmol) and 4-hydroxy-N-benzylpiperidine (105 g, 549 mmol) were heated together at 70° C. for 12 hours. The reaction mixture was then cooled to 50° C. and EtOH (1 L) was added; then 6M HCl (191 mL) was added slowly. The resulting mixture was then cooled to ambient temperature and ammonium formate (98.5 g, 1.56 mol) was added and then nitrogen gas was bubbled through the solution vigorously for 20 minutes. Palladium on activated carbon (20 g, 10 wt % dry basis) was then added and the reaction mixture was heated at 40° C. for 12 hours, and then filtered through a pad of Celite. The solvent was then removed under reduced pressure and 1M HCl (40 mL) was added to the crude residue. The pH of the mixture was then adjusted with 10 N NaOH to pH 12. The aqueous layer was extracted with ethyl acetate (2*150 mL) and the organic layer was dried (magnesium sulfate), filtered and the solvent removed under reduced pressure to give 155 g of the title intermediate (100% yield). HPLC (10-70) R_t=2.52; m/z: [M+H⁺] calcd for C₁₈H₂₀N₂O₂, 297.15; found, 297.3.

References:

US2006/205946,2006,A1 Location in patent:Page/Page column 22

4727-72-4 Synthesis