Acrylonitrile → N-(2-cyanoethyl)-4-aminopiperidine

HRID 1634061Notes

Reaction equation

HRID 1634061 reaction equation
FC(F)(F)C([NH:5][CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)=O.C(N(CC)CC)C.[C:21](#[N:24])[CH:22]=[CH2:23]>C1COCC1>[C:21]([CH2:22][CH2:23][N:9]1[CH2:8][CH2:7][CH:6]([NH2:5])[CH2:11][CH2:10]1)#[N:24]

Participants

5

Reactant 3

HCID 7855AcrylonitrileHCID 8471TriethylamineHCID 107742532,2,2-trifluoro-N-(piperidin-4-yl)acetamide

Product 1

HCID 22562162N-(2-cyanoethyl)-4-aminopiperidineYield 30%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3 g (15.3 mmol) of 4-trifluoroacetamidopiperidine, 3 g (4.25 mL, 30.6 mmol) of triethylamine, 3 mL (45.9 mmol) of acrylonitrile in 10 mL of THF was stirred at room temperature for 17 hr. The solvent and volatile were evaporated under reduced pressure. The residue was dissolved in 20 mL of methanol and 4 mL of 30% NH4OH and the solution was refluxed for 5 hr. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography on silica gel eluting first with 500 mL of dichloromethane, then 500 mL of 0.5% methanol/dichloromethane, followed by 1000 mL of 9:1:0.1 dichloromethane/methanol/ammonium hydroxide to give 0.7 g (30% yield) of the N-(2-cyanoethyl)-4-aminopiperidine.

Workup

  1. customThe solvent and volatile were evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in 20 mL of methanol
  3. temperature4 mL of 30% NH4OH and the solution was refluxed for 5 hr
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by column chromatography on silica gel eluting first with 500 mL of dichloromethane

Sources & evidence

ORD record
ord-88275e7a62004fc9ace308c9a0475af0
Source dataset
uspto-grants-2003_01
Patent number
US06506749B2

Reaction notes

Loading…