Propargyl bromide → 4-(2-Propyn-1-yl)morpholine

HRID 2377276Notes

Reaction equation

HRID 2377276 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[CH2:13](Br)[C:14]#[CH:15]>C(#N)C>[CH2:15]([N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1)[C:14]#[CH:13]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 8083MorpholineHCID 11430Potassium Carbonate

Product 1

HCID 4129414-(2-Propyn-1-yl)morpholine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of morpholine (0.78 mL, 8.98 mmol) and potassium carbonate (3.7 g, 26.9 mmol) in acetonitrile (10 mL) was added propargyl bromide (1.0 mL, 8.98 mmol) and the mixture was heated to about 80 C overnight. The reaction was quenched by addition of water and the mixture was extracted with diethyl ether. The combined organic extracts were washed with water, dried (Na2SO4), filtered and concentrated under vacuum to provide Example 639. 1H NMR (300 MHz, CD3OD) δ 2.57 (m, 4H) 2.68 (t, J=2.4 Hz, 1H) 3.29 (s, 2H) 3.70 (m, 4H).

Workup

  1. temperaturethe mixture was heated to about 80 C overnight
  2. customThe reaction was quenched by addition of water
  3. extractionthe mixture was extracted with diethyl ether
  4. washThe combined organic extracts were washed with water
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customto provide Example 639

Sources & evidence

ORD record
ord-a3aa7d94a36e4f189ab7030e47aec989
Source dataset
uspto-grants-2008_12
Patent number
US07468371B2

Reaction notes

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