Dichloromethane → 4-(2,3-Epoxypropyl)morpholine

HRID 1768581Notes

Reaction equation

HRID 1768581 reaction equation
[H-].[Na+].[NH:3]1[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.[CH2:9]([CH:11]1[O:13][CH2:12]1)Cl.C(Cl)Cl>O1CCCC1>[O:6]1[CH2:7][CH2:8][N:3]([CH2:9][CH:11]2[O:13][CH2:12]2)[CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7835EpichlorohydrinHCID 8083MorpholineHCID 24758Sodium hydride

Product 1

HCID 977514-(2,3-Epoxypropyl)morpholineYield 18.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.87 g (20 mmole) of sodium hydride (as a 55% w/w suspension in mineral oil) were suspended in 20 ml of tetrahydrofuran. 1.74 g (20 mmole) of morpholine and subsequently 1.85 g (20 mmole) of epichlorohydrin were then added, whilst ice-cooling, to this suspension, and the reaction mixture was allowed to stand at room temperature for 48 hours. At the end of this time, methylene chloride was added to the reaction mixture, and the organic layer was separated, washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and concentrated by evaporation under reduced pressure. The residue was purified by silica gel column chromatography (eluent: methylene chloride), to give 530 mg of 1-morpholino-2,3-epoxypropane.

Workup

  1. temperaturecooling, to this suspension
  2. customthe organic layer was separated
  3. washwashed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated by evaporation under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent: methylene chloride)

Sources & evidence

ORD record
ord-14838f2bec374c7881a95b01c9f3fd58
Source dataset
uspto-grants-1995_01
Patent number
US05378690

Reaction notes

Loading…