Hydrochloric Acid → 2-Methyl-1-morpholinopropan-2-ol

HRID 1251878Notes

Reaction equation

HRID 1251878 reaction equation
[O:1]=[C:2]([CH3:10])[CH2:3][N:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1.[CH3:11][Mg+].[Br-].Cl>C(OCC)C>[OH:1][C:2]([CH3:11])([CH3:10])[CH2:3][N:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 110299481-(4-Morpholinyl)acetoneHCID 178418689HCID 178418689, compound

Product 1

HCID 222731702-Methyl-1-morpholinopropan-2-olYield 33%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of N-(2-oxopropyl)morpholine (82 g, 0.57 mmol) in diethyl ether (400 ml) was added to a solution of 3M CH3MgBr (500 ml, 1.5 ml) in anhydrous diethyl ether (21) and stirred at 0° C. under an argon atmosphere. The mixture was stirred at ambient temperature for 16 hours, treated with 12N HCl (50 ml) and extracted with ethyl acetate. The product was purified by flash column chromatography eluting with ethyl acetate to give N-(2-hydroxy-2-methylpropyl)morpholine.

Workup

  1. stirringThe mixture was stirred at ambient temperature for 16 hours
  2. extractionextracted with ethyl acetate
  3. customThe product was purified by flash column chromatography
  4. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-200b45484e3d4c15b8008ffdc4d335ed
Source dataset
uspto-grants-2002_01
Patent number
US06342765B1

Reaction notes

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