Piperidine → 1-(But-3-yn-1-yl)piperidine

HRID 1619368Notes

Reaction equation

HRID 1619368 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Br[CH2:8][CH2:9][C:10]#[CH:11].C([O-])([O-])=O.[K+].[K+]>CC#N.O>[CH2:11]([N:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[CH2:10][C:9]#[CH:8]

Participants

6

Reactant 3

HCID 8082PiperidineHCID 11430Potassium CarbonateHCID 110734644-Bromobut-1-yne

Product 1

HCID 131559861-(But-3-yn-1-yl)piperidineYield 43.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of piperidine (2.9 g, 33.8 mmol), 4-bromobut-1-yne (5 g, 37.6 mmol) and K2CO3 (3 g, 2.2 mmol) in CH3CN was stirred at 80° C. for 2 h. After it was cooled to room temperature, the solution was diluted with H2O and extracted with ethyl acetate (3×200 mL). Then the combined organic layers were dried over Na2SO4 and concentrated to give 2 g of the crude product, which was directly used for the next step without further purification. MS (ESI): 138 (MH+).

Workup

  1. extractionextracted with ethyl acetate (3×200 mL)
  2. dry with materialThen the combined organic layers were dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-f9b7ea33b07a4db1a31e45147d9b6071
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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