3-Amino-α,α-dimethyl-3-phenyl-1-piperidineacetonitrile → HCID 59438452, compound

HRID 2177501Notes

Reaction equation

HRID 2177501 reaction equation
[NH2:1][C:2]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:7][CH2:6][CH2:5][N:4]([C:8]([CH3:12])([CH3:11])[C:9]#N)[CH2:3]1.C[Mg]Br>O1CCCC1.C(OCC)C>[C:8]([N:4]1[CH2:5][CH2:6][CH2:7][C:2]([NH2:1])([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:3]1)([CH3:12])([CH3:9])[CH3:11]

Participants

5

Reactant 2

HCID 594385233-Amino-α,α-dimethyl-3-phenyl-1-piperidineacetonitrileHCID 178418573HCID 178418573, compound

Product 1

HCID 59438452HCID 59438452, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 100 mg (0.411 mmol) rac-2-(3-Amino-3-phenyl-piperidin-1-yl)-2-methyl-propionitrile in 2.0 ml tetrahydrofuran over mol-sieve at 0° C. under nitrogen, was added dropwise 1.4 ul (4.11 mmol) of a 3M methylmagnesium bromide solution in diethyl ether. The mixture was stirred at 0° C. for 10 minutes, and then at 60° C. for 30 hours. The mixture was cooled in an ice bath and quenched with a saturated ammonium chloride solution. The mixture was extracted 3 times with ethyl acetate. The combined extracts were dried over sodium sulfate, filtered and concentrated in vacuo to provide 60 mg (63%) of the title compound as a yellow gum. MS (m/e): 233.2 (M+H).

Workup

  1. waitat 60° C. for 30 hours
  2. temperatureThe mixture was cooled in an ice bath
  3. customquenched with a saturated ammonium chloride solution
  4. extractionThe mixture was extracted 3 times with ethyl acetate
  5. dry with materialThe combined extracts were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-93bdf6b6a78843c7abb14a1d62a227b7
Source dataset
uspto-grants-2015_06
Patent number
US09067911B2

Reaction notes

Loading…