Methyl 1-benzyl-4-methyl-1,2,5,6-tetrahydropyridin-3-ylcarbamate → Methyl 1-benzyl-4-methylpiperidin-3-yl-carbamate

HRID 1853376Notes

Reaction equation

HRID 1853376 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH3:14])=[C:10]([NH:15][C:16](=[O:19])[O:17][CH3:18])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>CO.[Pt]=O>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH3:14])[CH:10]([NH:15][C:16](=[O:19])[O:17][CH3:18])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 58526548Methyl 1-benzyl-4-methyl-1,2,5,6-tetrahydropyridin-3-ylcarbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 53396489Methyl 1-benzyl-4-methylpiperidin-3-yl-carbamateYield 66%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

Platinum oxide (1.0 g, 4.41 mmol, 0.11 equiv.) was added to a solution of methyl 1-benzyl-4-methyl-1,2,5,6-tetrahydropyridin-3-ylcarbamate (10 g, 38.46 mmol, 1.00 equiv.) in methanol (200 mL). After introducing hydrogen gas, the mixture was stirred at about 60° C. for about 16 hours and then was filtered. The resulting filtrate was concentrated to give a crude residue that was then purified by silica gel column chromatography (ethyl acetate/petroleum (1:2)) to afford the title product a yellow solid (7 g; yield=66%). LC-MS: m/z=263 (M+H)+.

Workup

  1. filtrationwas filtered
  2. concentrationThe resulting filtrate was concentrated
  3. customto give a crude residue that
  4. customwas then purified by silica gel column chromatography (ethyl acetate/petroleum (1:2))

Sources & evidence

ORD record
ord-2b8d5b8dc6ae4097b00397967f567b71
Source dataset
uspto-grants-2015_02
Patent number
US08962638B2

Reaction notes

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