Ammonia → Tert-butyl 4-(2-amino-1-phenylethyl)piperidine-1-carboxylate

HRID 1943025Notes

Reaction equation

HRID 1943025 reaction equation
[C:1]([C:3]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[C:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1)#[N:2].N>C(O)C.[Ni].O>[NH2:2][CH2:1][CH:3]([CH:4]1[CH2:5][CH2:6][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:8][CH2:9]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 2

HCID 222Ammonia2×HCID 44122578Tert-butyl 4-(cyano(phenyl)methylene)piperidine-1-carboxylate

Product 1

HCID 58415947Tert-butyl 4-(2-amino-1-phenylethyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 3

HCID 935NickelCatalyst2×HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

tert-butyl 4-[cyano(phenyl)methylene]piperidine-1-carboxylate (1.18 g, 3.95 mmol) in ethanol (15 ml) was saturated with NH3 at ambient temperature and Raney nickel (1 ml, 3.95 mmol) in water was added. The reaction was placed on a Parr reactor under H2 pressure (48 psi) for 19 hours. The reaction mixture was then re-saturated with NH3 and additional Raney nickel (1 ml, 3.95 mmol) was added before placing back on the Parr reactor for an additional 5.5 hours. The reaction mixture was filtered through Celite, washing with EtOH, and concentrated in vacuo. The product was carried on without further purification.

Workup

  1. customfor 19 hours
  2. filtrationThe reaction mixture was filtered through Celite
  3. washwashing with EtOH
  4. concentrationconcentrated in vacuo
  5. customThe product was carried on without further purification

Sources & evidence

ORD record
ord-ab0346fb6807451ebe1ee52b8b17c723
Source dataset
uspto-grants-2013_03
Patent number
US08389720B2

Reaction notes

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