methyl 2-[(E)-2-phenylvinyl]isonicotinate → Methyl 2-(2-cyclohexylethyl)piperidine-4-carboxylate

HRID 383917Notes

Reaction equation

HRID 383917 reaction equation
[C:1]1(/[CH:7]=[CH:8]/[C:9]2[CH:10]=[C:11]([CH:16]=[CH:17][N:18]=2)[C:12]([O:14][CH3:15])=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>Cl.CO.[Pt]=O>[CH:1]1([CH2:7][CH2:8][CH:9]2[CH2:10][CH:11]([C:12]([O:14][CH3:15])=[O:13])[CH2:16][CH2:17][NH:18]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 1

HCID 59291512methyl 2-[(E)-2-phenylvinyl]isonicotinate

Product 1

HCID 59291261Methyl 2-(2-cyclohexylethyl)piperidine-4-carboxylate

Reagents, catalysts & solvents 3

HCID 82844Platinum oxide (PtO)CatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

To a solution of methyl 2-[(E)-2-phenylvinyl]isonicotinate in hydrochloric acid and MeOH was added platinum oxide, followed by stirring at room temperature for 8 hours under a hydrogen atmosphere of 3 atm. The reaction mixture was filtered through Celite, and the filtrate was then concentrated under reduced pressure. To the residue were added an aqueous Na2CO3 solution and xylene, and the aqueous layer was extracted with CHCl3. The organic layer was dried over MgSO4 and then concentrated under reduced pressure to obtain methyl 2-(2-cyclohexylethyl)piperidine-4-carboxylate as a colorless oily substance.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe filtrate was then concentrated under reduced pressure
  3. additionTo the residue were added an aqueous Na2CO3 solution and xylene
  4. extractionthe aqueous layer was extracted with CHCl3
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cb895025838c4e5a974f502e8bd0dc88
Source dataset
uspto-grants-2013_02
Patent number
US08367696B2

Reaction notes

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