HCID 18997146, compound → HCID 18997131, compound

HRID 1708048Notes

Reaction equation

HRID 1708048 reaction equation
[Br-].[C:2]1([CH2:8][CH2:9][N+:10]2[CH:15]=[CH:14][C:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:12][CH:11]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Pt](=O)=O.CO>[C:2]1([CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][CH:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:12][CH2:11]2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 18997146HCID 18997146, compound

Product 1

HCID 18997131HCID 18997131, compoundYield 89.9%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

A mixture of 5.90 g (17.5 mmol) of 1-(2-phenylethyl)-4-carboethoxypyridinium bromide, 0.60 g of platinum (IV) oxide and 100 mL of methanol was hydrogenated at 50 p.s.i. and room temperature for 1.5 hours. The reaction mixture was filtered, concentrated and the residue dissolved in water. The aqueous solution was made alkaline to pH 9-10 with aqueous potassium carbonate and extracted with ethyl acetate. The organic extracts were washed with saturated sodium bicarbonate solution, saturated sodium chloride solution, dried and evaporated to afford 4.11 g of 1-(2-phenylethyl)-4-carboethoxypiperidine as a yellow oil. NMR (CDCl3) δ7.16-7.32 (m, 5H); 4.08-4.19 (q, 2H); 2.91-3.02 (m, 2H); 2.77-2.88 (m, 2H); 2.53-2.65 (m, 2H); 2.23-2.35 (m, 1H); 2.03-2.15 (m, 2H); 1.87-1.98 (m, 2H); 1.72-1.88 (m, 4H); 1.20-1.30 (t, 3H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. dissolutionthe residue dissolved in water
  4. extractionextracted with ethyl acetate
  5. washThe organic extracts were washed with saturated sodium bicarbonate solution, saturated sodium chloride solution
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-581f96a5359042bd973082b51e1b23ad
Source dataset
uspto-grants-1994_10
Patent number
US05356906

Reaction notes

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