Morpholine → 4-Dodecylmorpholine

HRID 1655138Notes

Reaction equation

HRID 1655138 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[CH2:13](Br)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].[H][H]>CC(C)=O>[CH2:24]([N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH3:13]

Participants

6

Reactant 4

HCID 8083MorpholineHCID 89191-BromododecaneHCID 11430Potassium CarbonateHCID 178418361HCID 178418361, compound

Product 1

HCID 737644-Dodecylmorpholine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

174.2 g of morpholine (1 mole), 69 g of potassium carbonate (0.5 mole) and 300 mL of acetone were heated to reflux. To the above solution 124.5 g (0.5 mole) of dodecylbromide were added dropwise. After the addition was complete, the reaction mixture was heated at reflux for four hours. The reaction mixture was filtered, and the solvent evaporated in vacuo to leave an oil, which was distilled under vacuum to give a colorless liquid. Yield is 112.9 g (90% of the theory). Proton NMR δ0.8 (S,3Hz), 1.2 (M, 22Hz), 2.3 (M,4Hz) and 3.5 (M,4Hz). Elemental analysis, observed (theory) is carbon 74.96 (75.25), hydrogen 13.21 (13.02), and nitrogen 5.38 (5.48). Close proximity between the observed and theoretical values indicates the positive identification of this compound. Similarly prepared compounds are shown in Table I:

Workup

  1. additionAfter the addition
  2. temperaturethe reaction mixture was heated
  3. temperatureat reflux for four hours
  4. filtrationThe reaction mixture was filtered
  5. customthe solvent evaporated in vacuo
  6. customto leave an oil, which
  7. distillationwas distilled under vacuum
  8. customto give a colorless liquid
  9. customClose proximity between the

Sources & evidence

ORD record
ord-d5d6b82b65e3400c89b115376d1e5010
Source dataset
uspto-grants-1993_10
Patent number
US05250194

Reaction notes

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