Morpholine → Morpholine, 4-tetradecyl-

HRID 258243

Reaction equation

HRID 258243 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].[NH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1>C(#N)C>[CH2:2]([N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 8208Myristyl bromide

Product 1

HCID 117616Morpholine, 4-tetradecyl-Yield 94%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a 250-mL round bottom flask, equipped with a magnetic stirrer, a heating mantle and reflux condenser, were placed 1-bromotetradecane (15.9 g, 57.3 mmol), acetonitrile (75 mL), and morpholine (10 g, 114.7 mmol). The reaction mixture was refluxed for 4 hrs. The reaction mixture was cooled to room temperature and was concentrated to a residue on a rotary evaporator. Water and ethyl acetate were added. The organic phase was separated and washed with saturated sodium chloride solution, and then dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated to dryness affording 15.2 g (94% yield) of 4-tetradecylmorpholine as a tan oil. This intermediate was subjected to the next step without further purification.

Workup

  1. customIn a 250-mL round bottom flask, equipped with a magnetic stirrer
  2. temperaturea heating mantle and reflux condenser
  3. temperatureThe reaction mixture was refluxed for 4 hrs
  4. concentrationwas concentrated to a residue on a rotary evaporator
  5. additionWater and ethyl acetate were added
  6. customThe organic phase was separated
  7. washwashed with saturated sodium chloride solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationAfter filtration
  10. customthe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-4915d56f036b428187c79fe574ec5742
Source dataset
uspto-grants-1993_11
Patent number
US05266567

Linked notes

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