Water → 4-(4-Butylpiperidin-1-YL)butanenitrile

HRID 1859619Notes

Reaction equation

HRID 1859619 reaction equation
[CH2:1]([CH:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4].Br[CH2:12][CH2:13][CH2:14][C:15]#[N:16].C(=O)([O-])[O-].[K+].[K+].O>C(#N)C.CCCCCCC.CCOC(C)=O>[CH2:1]([CH:5]1[CH2:10][CH2:9][N:8]([CH2:12][CH2:13][CH2:14][C:15]#[N:16])[CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 214124-BromobutyronitrileHCID 132838674-Butylpiperidine

Product 1

HCID 186263854-(4-Butylpiperidin-1-YL)butanenitrileYield 87%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 21899848Ethylacetate heptaneSolvent

Procedure

In a 100 mL flask with a magnetic stirrer was placed 3 (2.3 g, 16.4 mmol), 4-bromobutyronitrile (2.4 g, 16.4 mmol), potassium carbonate powder (2.5 g, 18 mmol) in acetonitrile (20 mL). The reaction mixture was stirred at rt for 5 h followed by addition of H2O (15 mL). The mixture was extracted with ethyl acetate (3×30 mL) and the combined organic phases were evaporated to dryness to produce 3.9 of crude 4. The crude product was subjected to CC [eluent: heptane: EtOAc (1:1)] to give pure 4 (2.3 g, 87%). 1H NMR (CDCl3) δ 0.82 (t, 3H), 1.19-1.37 (m, 9H), 1.64-1.75 (d, 2H), 1.84-2.01 (m, 4H), 2.39-2.54 (m, 4H), 2.89-2.97 (d, 2H).

Workup

  1. customIn a 100 mL flask with a magnetic stirrer was placed
  2. extractionThe mixture was extracted with ethyl acetate (3×30 mL)
  3. customthe combined organic phases were evaporated to dryness
  4. customto produce 3.9 of crude 4

Sources & evidence

ORD record
ord-0e5b03615e1b43b995548fbcf347340e
Source dataset
uspto-grants-2003_03
Patent number
US06528529B1

Reaction notes

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