Tert-butyl 4-(aminomethyl)-4-phenylpiperidine-1-carboxylate → HCID 18318102, compound

HRID 1800827Notes

Reaction equation

HRID 1800827 reaction equation
[NH2:1][CH2:2][C:3]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1.[H][H]>C(O)C.O=[Pt]=O>[NH2:1][CH2:2][C:3]1([CH:16]2[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]2)[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1

Participants

5

Reactant 2

HCID 10565452Tert-butyl 4-(aminomethyl)-4-phenylpiperidine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 18318102HCID 18318102, compoundYield 64.7%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

Tert-butyl 4-(aminomethyl)-4-phenylpiperidine-1-carboxylate (355 mg, 1.22 mmol) and 1.15 g PtO2 (5.1 mmol) in 125 ml ethanol were shaked in PARR apparatus under 60 psi of hydrogen for 20 hours. Celite was loaded on top of an ion exchange cartridge (MCX, Phenomenex, 6 g adsorbent). The crude reaction slurry was filtered through this set-up, the pyrophoric catalyst washed with ethanol and water and removed. The cartridge was washed with methanol and then the product eluted with a 2 M solution of NH3 in MeOH. The eluent was concentrated to give 234 mg of the title compound as an oil.

Workup

  1. customThe crude reaction slurry
  2. filtrationwas filtered through this set-up
  3. washthe pyrophoric catalyst washed with ethanol and water
  4. customremoved
  5. washThe cartridge was washed with methanol
  6. washthe product eluted with a 2 M solution of NH3 in MeOH
  7. concentrationThe eluent was concentrated

Sources & evidence

ORD record
ord-79b65f2b752143eeac49119228007a59
Source dataset
uspto-grants-2013_01
Patent number
US08343999B2

Reaction notes

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