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

HRID 268619Notes

Reaction equation

HRID 268619 reaction equation
C(OS([C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=CC=1)(=O)=O)CC#C.[NH:16]1C[CH2:20][CH2:19][CH2:18][CH2:17]1.C(=O)([O-])[O-].[K+].[K+]>C(O)C.O>[CH2:17]([N:16]1[CH2:15][CH2:12][CH2:13][CH2:14][CH2:9]1)[CH2:18][C:19]#[CH:20]

Participants

6

Reactant 3

HCID 8082PiperidineHCID 11430Potassium CarbonateHCID 2720203-Butynyl p-toluenesulfonate

Product 1

HCID 131559861-(But-3-yn-1-yl)piperidine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A solution of toluene-4-sulfonic acid but-3-ynyl ester (45.0 g) and piperidine (40 mL) in ethanol (70 mL) was treated with a solution of potassium carbonate (27.8 g) in water (70 mL). The mixture was heated to 80° C. for 2 h, cooled to RT, and extracted with DCM (3×100 mL). The combined organic phases were dried (magnesium sulfate), and evaporated. Distillation of the residue (110° C., 30 mm Hg) gave the title compound as a colorless oil (17.3 g).

Workup

  1. temperaturecooled to RT
  2. extractionextracted with DCM (3×100 mL)
  3. dry with materialThe combined organic phases were dried (magnesium sulfate)
  4. customevaporated
  5. distillationDistillation of the residue (110° C., 30 mm Hg)

Sources & evidence

ORD record
ord-ebaa0745af3846c8a7c27067838dbd56
Source dataset
uspto-grants-2008_11
Patent number
US07446104B2

Reaction notes

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