Hydrochloric Acid → 6,6-Dimethyl-2-phenyl-piperidin-3-ylamine

HRID 1244081Notes

Reaction equation

HRID 1244081 reaction equation
[CH3:1][C:2]1([CH3:17])[CH2:7][CH2:6][CH:5]([N+:8]([O-])=O)[CH:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[NH:3]1.Cl>C1COCC1.[Zn]>[CH3:1][C:2]1([CH3:17])[NH:3][CH:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:5]([NH2:8])[CH2:6][CH2:7]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 219317842,2-Dimethyl-5-nitro-6-phenyl-piperidine

Product 1

HCID 99644056,6-Dimethyl-2-phenyl-piperidin-3-ylamineYield 69%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To 2,2-Dimethyl-5-nitro-6-phenyl-piperidine in 0.4 mL of THF was added 0.2 mL of 6 M HCl and 100 mg (1.5 mmol) of zinc powder. The mixture was stirred at rt until complete by TLC analysis. The mixture was filtered through celite, rinsing with 5 mL of water. The aqueous solution was washed with Et2O (3×5 mL) and was then basified with 1 N NaOH to pH=12. The mixture was extracted with CHCl3 and the extracts were dried via filtration through a plug of cotton and concentrated to give 6 mg (69%) of the title compound as a colorless oil: mass spectrum m/e=205 (M+1)

Workup

  1. filtrationThe mixture was filtered through celite
  2. washrinsing with 5 mL of water
  3. washThe aqueous solution was washed with Et2O (3×5 mL)
  4. extractionThe mixture was extracted with CHCl3
  5. customthe extracts were dried via filtration through a plug of cotton
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-100f70a7dd514e679dc4fb867ab08a1e
Source dataset
uspto-grants-2006_10
Patent number
US07119207B2

Reaction notes

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