Hydrochloric Acid → HCID 18997139, compound

HRID 1708051Notes

Reaction equation

HRID 1708051 reaction equation
[C:1]1([CH2:7][CH2:8][N:9]2[CH2:14][CH2:13][C:12]([CH3:18])([CH:15]=[N:16]O)[CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl>[Pt](=O)=O.CO>[C:1]1([CH2:7][CH2:8][N:9]2[CH2:14][CH2:13][C:12]([CH3:18])([CH2:15][NH2:16])[CH2:11][CH2:10]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86748191HCID 86748191, compound

Product 1

HCID 18997139HCID 18997139, compoundYield 78.9%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

A mixture containing 0.58 g (2.4 mmol) of 1-(2-phenylethyl)-4-methyl-4-oximinomethylpiperidine, 100 mL of methanol, 80 mg of platinum (IV) oxide and 0.75 mL of concentrated hydrochloric acid was hydrogenated at 40 p.s.i. for 2 hours. The mixture was filtered and evaporated. The residue was dissolved in water and made alkaline with aqueous potassium carbonate. The aqueous mixture was extracted with methylene chloride. The organic extracts were dried and evaporated to give 0.44 g of 1-(2-phenylethyl) -4-methyl-4-aminomethylpiperidine. NMR (CDCl3) δ7.18-7.28 (m, 5H); 5.22- 5.45 (br, 2H); 2.89 (s, 2H); 2.78-2.88 (m, 2H); 2.55-2.67 (m, 2H); 2.19 (t, 2H); 1.51-1.78 (m, 4H); 1.27-1.49 (m, 2H); 0.98 (s, 3H).

Workup

  1. filtrationThe mixture was filtered
  2. customevaporated
  3. dissolutionThe residue was dissolved in water
  4. extractionThe aqueous mixture was extracted with methylene chloride
  5. customThe organic extracts were dried
  6. customevaporated

Sources & evidence

ORD record
ord-83bf5275e5654288ad2a6e7b22532a3a
Source dataset
uspto-grants-1994_10
Patent number
US05356906

Reaction notes

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