Ethyl 5-benzylnicotinate → Ethyl 5-(cyclohexylmethyl)piperidine-3-carboxylate

HRID 253101Notes

Reaction equation

HRID 253101 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[C:5]1[CH:10]=[C:9]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:8]=[N:7][CH:6]=1)[CH3:2]>CCO.Cl.O=[Pt]=O>[CH:12]1([CH2:11][CH:9]2[CH2:8][NH:7][CH2:6][CH:5]([C:4]([O:3][CH2:1][CH3:2])=[O:18])[CH2:10]2)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1

Participants

5

Reactant 1

HCID 66610002Ethyl 5-benzylnicotinate

Product 1

HCID 66844627Ethyl 5-(cyclohexylmethyl)piperidine-3-carboxylateYield 73%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

A suspension of ethyl-5-benzylnicotinate (1.0 g, 4.1 mmol) and PtO2 (800 mg) in EtOH (25 mL) and HCl (conc., 5.0 mL) was mixed in a Parr shaker under 40 psi of H2 for 2 hours. The mixture was filtered through celite and concentrated to about 10% of the original volume. The resulting mixture was extracted with CH2Cl2 (3×30 mL). The organic layer was concentrated under reduced pressure to furnish the title compound (755 mg, 73% yield) as a white solid. MS m/z: 254.3 (M+1).

Workup

  1. additionwas mixed in a Parr shaker under 40 psi of H2 for 2 hours
  2. filtrationThe mixture was filtered through celite and
  3. concentrationconcentrated to about 10% of the original volume
  4. extractionThe resulting mixture was extracted with CH2Cl2 (3×30 mL)
  5. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-32c156fd940f498890066107f181b7d7
Source dataset
uspto-grants-2011_01
Patent number
US07872009B2

Reaction notes

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