Formaldehyde → 4-Morpholinobut-2-YN-1-OL

HRID 2288193Notes

Reaction equation

HRID 2288193 reaction equation
[CH2:1]=O.[NH:3]1[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.S(=O)(=O)(O)O.[CH2:14]([OH:17])[C:15]#[CH:16].[I-].[K+]>S([O-])([O-])(=O)=O.[Cu+2]>[O:6]1[CH2:7][CH2:8][N:3]([CH2:1][C:16]#[C:15][CH2:14][OH:17])[CH2:4][CH2:5]1

Participants

7

Reactant 5

HCID 712FormaldehydeHCID 1118Sulfuric AcidHCID 4875Potassium IodideHCID 7859Propargyl alcoholHCID 8083Morpholine

Product 1

HCID 31128494-Morpholinobut-2-YN-1-OL

Reagents, catalysts & solvents 1

HCID 24462Copper SulfateCatalyst

Conditions

Temperature
95 °C

Procedure

A mixture of formaldehyde (37% in water, 20.7 ml) and morpholine (17.1 ml) was adjusted to pH 3.5 with diluted sulfuric acid. Propargyl alcohol (10 g), potassium iodide (0.3 g), and copper (II) sulfate (0.14 g) were added to the solution and the whole was stirred at 95° C. for 6 hours. After cooling, the insoluble material was removed by filtration and the pH of the filtrate was adjusted to 9 with 24% sodium hydroxide solution. Brine (100 ml) was added to the solution and the solution was extracted with a mixture of ethyl acetate and ethanol (10:1) eight times and then with n-butanol six times. The combined extract was dried over magnesium sulfate and evaporated in vacuo. The residue was distilled in reduced pressure to give 4-morpholino-2-butyn-1-ol (14.03 g).

Workup

  1. temperatureAfter cooling
  2. customthe insoluble material was removed by filtration
  3. additionBrine (100 ml) was added to the solution
  4. extractionthe solution was extracted with a mixture of ethyl acetate and ethanol (10:1) eight times
  5. extractionThe combined extract
  6. dry with materialwas dried over magnesium sulfate
  7. customevaporated in vacuo
  8. distillationThe residue was distilled in reduced pressure

Sources & evidence

ORD record
ord-d3399c54380d42d7a19ba6fff95e00c7
Source dataset
uspto-grants-2000_07
Patent number
US06087357

Reaction notes

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