Potassium Iodide → 1,1-Dimethylethyl 4-[(cyanomethyl)ethylamino]-1-piperidinecarboxylate

HRID 2301186Notes

Reaction equation

HRID 2301186 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][CH2:15][CH3:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[CH2:18][C:19]#[N:20].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>ClCCCl.C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([N:14]([CH2:18][C:19]#[N:20])[CH2:15][CH3:16])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 18374730tert-Butyl 4-(ethylamino)piperidine-1-carboxylate

Product 1

HCID 183747091,1-Dimethylethyl 4-[(cyanomethyl)ethylamino]-1-piperidinecarboxylateYield 65.5%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 150 mg 1-t-butyloxycarbonyl-4-ethylamino-piperidine (from Step A) in 3 ml DCE were added 60 mg of chloroacetonitrile, 109 mg of potassium carbonate, and 11 mg of potassium iodide. The reaction was stirred at 60° C. overnight. Methylene chloride was added, and the solution was washed with 2×20 ml water, and 20 ml brine. The solvent was then evaporated under reduced pressure. The residue was purified by flash chromatography with 20% EtOAc in hexane to give 115 mg of the title compound.

Workup

  1. washthe solution was washed with 2×20 ml water, and 20 ml brine
  2. customThe solvent was then evaporated under reduced pressure
  3. customThe residue was purified by flash chromatography with 20% EtOAc in hexane

Sources & evidence

ORD record
ord-fba84c21a1694e8d908156b838c098e0
Source dataset
uspto-grants-2002_12
Patent number
US06498161B1

Reaction notes

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