Morpholine → 4-(2-Propyn-1-yl)morpholine

HRID 2297499Notes

Reaction equation

HRID 2297499 reaction equation
[CH2:1](OS(C)(=O)=O)[C:2]#[CH:3].[NH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1.C([O-])([O-])=O.[Na+].[Na+]>C(O)C>[CH2:3]([N:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)[C:2]#[CH:1]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 10340Sodium CarbonateHCID 305925propargyl mesylate

Product 1

HCID 4129414-(2-Propyn-1-yl)morpholineYield 120.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of methanesulfonic acid prop-2-ynyl ester (3.44 g, 25.7 mmoles), prepared as described in example 136, morpholine (5.4 g) and Na2CO3 (3.3 g, 30.84 mmoles) in ethanol was stirred at room temperature for 6 hours. The solid was filtered off and the solution was concentrated and poured into water. The mixture was acidified with HCl, extracted with ethyl ether, alkalinised with NaHCO3 and extracted with ethyl acetate. The organic phase was anhydrified over Na2SO4 and dried to give 3.87 g of the title compound which was used as such in the subsequent step.

Workup

  1. customprepared
  2. filtrationThe solid was filtered off
  3. concentrationthe solution was concentrated
  4. additionpoured into water
  5. extractionextracted with ethyl ether
  6. extractionextracted with ethyl acetate
  7. customdried

Sources & evidence

ORD record
ord-bd85d9f135b64e09b1cb8ffee13e9baa
Source dataset
uspto-grants-2002_12
Patent number
US06492360B1

Reaction notes

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