Potassium Carbonate → Morpholine, 4-(4-chloro-2-butyn-1-yl)-3-ethyl-, (3R)-

HRID 584237Notes

Reaction equation

HRID 584237 reaction equation
Cl.[CH2:2]([C@@H:4]1[CH2:9][O:8][CH2:7][CH2:6][NH:5]1)[CH3:3].[Cl:10][CH2:11][C:12]#[C:13][CH2:14]Cl.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:10][CH2:11][C:12]#[C:13][CH2:14][N:5]1[CH2:6][CH2:7][O:8][CH2:9][C@H:4]1[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 131821,4-Dichloro-2-butyneHCID 60146101(3R)-3-Ethylmorpholine--hydrogen chloride (1/1)

Product 1

HCID 54431099Morpholine, 4-(4-chloro-2-butyn-1-yl)-3-ethyl-, (3R)-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (3R)-3-ethylmorpholine hydrochloride (0.2 g), 1,4-dichloro-2-butyne (0.5 ml) and potassium carbonate (0.71 g) in N,N-dimethylformamide (10 ml) was stirred at room temperature for 2 hours. After removal of the solvent, ethyl acetate and sodium hydrogen carbonate solution were added thereto. The organic layer was separated and the aqueous layer was extracted with ethyl acetate twice. The combined organic layer was dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel with a mixture of ethyl acetate and n-hexane (1:1) as an eluent to give (3R)-4-(4-chloro-2-butynyl)-3-ethylmorpholine (0.2 g) as an oil.

Workup

  1. customAfter removal of the solvent, ethyl acetate and sodium hydrogen carbonate solution
  2. additionwere added
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with ethyl acetate twice
  5. dry with materialThe combined organic layer was dried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by column chromatography on silica gel with a mixture of ethyl acetate and n-hexane (1:1) as an eluent

Sources & evidence

ORD record
ord-f6a537e5636f4fd5940642f6e1b2bf35
Source dataset
uspto-grants-2005_08
Patent number
US06924278B2

Reaction notes

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