Morpholine → 4-Morpholinebutanamide, N-methoxy-N-methyl-

HRID 1986388Notes

Reaction equation

HRID 1986388 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]([N:7]([CH3:10])[O:8][CH3:9])=[O:6].C([O-])([O-])=O.[K+].[K+].[NH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1>CC#N>[CH3:10][N:7]([O:8][CH3:9])[C:5](=[O:6])[CH2:4][CH2:3][CH2:2][N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 112522004-chloro-N-methoxy-N-methylbutyramide

Product 1

HCID 113903034-Morpholinebutanamide, N-methoxy-N-methyl-Yield 44.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
105 °C

Procedure

To a solution of the product from Step 1 (3.01 g, 18.1 mmol) in MeCN (40 mL), was added K2CO3 (10 g, 72.4 mmol) and morpholine (1.58 mL, 18.1 mmol). This mixture was then heated to 105° C. in a sealed tube for overnight. The reaction mixture then diluted with MeCN (50 mL), then filtered and concentrated. Residue was taken up in Et2O (100 mL), washed with brine, dried over Na2SO4, filtered and concentrated to afford the title compound as a colorless oil (1.73 g, 44%), which was used directly to next step without further purification. MS (ES+) m/e 217 [M+H]+.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f5949b362bd04e0aa6ab015cd81d25e2
Source dataset
uspto-grants-2009_06
Patent number
US07547779B2

Reaction notes

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