Morpholine → Methyl 6-morpholin-4-yl-6-oxohexanoate

HRID 1820927Notes

Reaction equation

HRID 1820927 reaction equation
[C:1]([O:10][CH3:11])(=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([O-:8])=O.[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.Cl.C(N=C=NCCCN(C)C)C.C(N(CC)CC)C>C(Cl)(Cl)Cl>[N:12]1([C:6](=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2][C:1]([O:10][CH3:11])=[O:9])[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 8083MorpholineHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 6994472Methyl adipate

Product 1

HCID 23088646Methyl 6-morpholin-4-yl-6-oxohexanoateYield 100.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Monomethyl adipate (3.20 g) is dissolved in chloroform (70 ml), and thereto are added morpholine (2.61 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (5.75 g) and triethylamine (3.04 g) under ice-cooling. The mixture is then stirred at room temperature for 19 hours. Ice-water is added to the reaction solution and the mixture is extracted with chloroform. The organic layer is washed successively with 10% hydrochloric acid, a saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over sodium sulfate. The solvent is removed by evaporation under reduced pressure to give methyl 6-morpholin-4-yl-6-oxohexanoate (4.63 g). APCI-MS M/Z:230[M+H]+

Workup

  1. temperaturecooling
  2. extractionthe mixture is extracted with chloroform
  3. washThe organic layer is washed successively with 10% hydrochloric acid
  4. dry with materiala saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over sodium sulfate
  5. customThe solvent is removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-b2a06524ea34481c81dab1aeb5723d08
Source dataset
uspto-grants-2009_10
Patent number
US07605158B2

Reaction notes

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