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

HRID 2268931Notes

Reaction equation

HRID 2268931 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-2c15b7b5c0314ac4b31d4f7f5d1e22d5
Source dataset
uspto-grants-2001_12
Patent number
US06329370B1

Reaction notes

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