Hydrochloric Acid → HCID 69054070, compound

HRID 1727193Notes

Reaction equation

HRID 1727193 reaction equation
[CH3:1][C:2]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:7][CH2:6][CH2:5][NH:4][CH2:3]1.[ClH:14]>CO.C(OCC)C.[Pt](=O)=O>[ClH:14].[CH:8]1([C:2]2([CH3:1])[CH2:7][CH2:6][CH2:5][NH:4][CH2:3]2)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1

Participants

6

Reactant 2

HCID 313Hydrochloric Acid2×HCID 892083-Methyl-3-phenylpiperidine

Product 1

HCID 69054070HCID 69054070, compoundYield 66%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 3-methyl-3-phenylpiperidine (500 mg, 2.85 mmol) in methanol (8 ml) was added concentrated hydrochloric acid (1 ml) and platinum (IV) oxide (500 mg). The reaction mixture was hydrogenated at 50 psi for 3 h before filtering through Celite® and concentrating. The crude residue was dissolved in dichloromethane and washed with sodium carbonate and concentrated to give a crude semi solid. The crude product was dissolved in diethyl ether (15 ml) and methanol (5 ml) and hydrogen chloride (1M in diethyl ether, 30 ml) was added to afford a white solid which was filtered to give the pure product (0.41 g, 66%).

Workup

  1. filtrationbefore filtering through Celite®
  2. concentrationconcentrating
  3. dissolutionThe crude residue was dissolved in dichloromethane
  4. washwashed with sodium carbonate
  5. concentrationconcentrated
  6. customto give a crude semi solid
  7. customto afford a white solid which
  8. filtrationwas filtered

Sources & evidence

ORD record
ord-82b3308e4f814340bde223bb69d330e3
Source dataset
uspto-grants-2009_02
Patent number
US07494992B2

Reaction notes

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