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

HRID 1527795Notes

Reaction equation

HRID 1527795 reaction equation
[CH2:1](Br)[C:2]#[CH:3].C([O-])([O-])=O.[Cs+].[Cs+].[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1>CC(C)=O>[CH2:1]([N:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1)[C:2]#[CH:3]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 8083MorpholineHCID 10796Cesium carbonate

Product 1

HCID 4129414-(2-Propyn-1-yl)morpholineYield 95.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a stirred solution of propargyl bromide (50 g, 420 mmol) in acetone (300 mL), Cs2CO3 (136.5 g, 420 mmol) was added at 0° C. Then morpholine (36.60 g, 420 mmol) in acetone (200 mL) was added dropwise and reaction was stirred at room temperature for 16 h. On completion, the reaction mass was filtered and the filtrate was concentrated under reduced pressure to afford the title compound (50 g, crude). The isolated compound was used directly in the subsequent coupling step without further purification.

Workup

  1. customreaction
  2. filtrationOn completion, the reaction mass was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b464d463bf5442a19c178f8c549347fd
Source dataset
uspto-grants-2015_07
Patent number
US09089575B2

Reaction notes

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