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

HRID 1469162Notes

Reaction equation

HRID 1469162 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-1772eabfeca7438f89f6bd0ed64def5d
Source dataset
uspto-grants-2015_04
Patent number
US09006242B2

Reaction notes

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