Morpholine → Ethyl 4-(morpholin-4-yl)butanoate

HRID 336345Notes

Reaction equation

HRID 336345 reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[NH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1>CC#N>[CH2:8]([O:7][C:5](=[O:6])[CH2:4][CH2:3][CH2:2][N:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1)[CH3:9]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 76300Ethyl 4-bromobutyrate

Product 1

HCID 13191881Ethyl 4-(morpholin-4-yl)butanoateYield 96%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

A solution of ethyl 4-bromobutyrate (681 mg) in MeCN (5.0 mL) was treated with morpholine (0.61 mL) at rt. The reaction mixture was heated to 80° C. for 3 h and cooled down to rt. It was concentrated under reduced pressure, diluted with EA and the org. layer was washed with water and brine, dried over MgSO4, filtered and concentrated under reduced pressure. The title compound was obtained, without additional purification, as a yellow oil (643 mg; 96% yield).

Workup

  1. temperaturecooled down to rt
  2. concentrationIt was concentrated under reduced pressure
  3. additiondiluted with EA
  4. washlayer was washed with water and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-443901f9846f400e8c294099fa9aa396
Source dataset
uspto-grants-2014_11
Patent number
US08889676B2

Reaction notes

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