Acetone → 3-Amino-α,α-dimethyl-3-phenyl-1-piperidineacetonitrile

HRID 2177500Notes

Reaction equation

HRID 2177500 reaction equation
[C:1]1([C:7]2([NH2:13])[CH2:12][CH2:11][CH2:10][NH:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:14][C:15]([CH3:17])=O.C[Si]([C:22]#[N:23])(C)C.[OH-].[Na+]>C(O)(=O)C.ClCCl>[NH2:13][C:7]1([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:12][CH2:11][CH2:10][N:9]([C:15]([CH3:17])([CH3:14])[C:22]#[N:23])[CH2:8]1

Participants

7

Reactant 4

HCID 180AcetoneHCID 14798Sodium HydroxideHCID 82115Trimethylsilyl cyanideHCID 594385061236302-98-9

Product 1

HCID 594385233-Amino-α,α-dimethyl-3-phenyl-1-piperidineacetonitrileYield 76.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 300 mg (1.701 mmol) rac-3-Phenyl-piperidin-3-ylamine in 1.3 ml acetic acid, was added dropwise 188 ul (2.553 mmol) acetone. The mixture was stirred at room temperature for 5 minutes. 320 ul (2.553 mmol) trimethylsilyl cyanide was added dropwise. The temperature rose to 31° C. The mixture was stirred at room temperature for 4 hours. The mixture was diluted with dichloromethane and cooled to 0° C. NaOH 2N was added dropwise to basify the mixture. The organic layer was separated and the aqueous layer was extracted twice with dichloromethane. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo to provide 315 mg (76.1%) of the title compound as a yellow oil.

Workup

  1. customrose to 31° C
  2. stirringThe mixture was stirred at room temperature for 4 hours
  3. temperaturecooled to 0° C
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted twice with dichloromethane
  6. dry with materialThe combined organic layers were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cb1bae700b2a45db91f39a283af33159
Source dataset
uspto-grants-2015_06
Patent number
US09067911B2

Reaction notes

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