Morpholine → Methyl 4-morpholinocyclohex-3-enecarboxylate

HRID 594941

Reaction equation

HRID 594941 reaction equation
O=[C:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH3:11])=[O:9])[CH2:4][CH2:3]1.[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1>C1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[O:15]1[CH2:16][CH2:17][N:12]([C:2]2[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH3:11])=[O:9])[CH2:4][CH:3]=2)[CH2:13][CH2:14]1

Participants

5

Reactant 2

HCID 8083MorpholineHCID 226643Methyl 4-oxocyclohexanecarboxylate

Product 1

HCID 12484393Methyl 4-morpholinocyclohex-3-enecarboxylateYield 88.9%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 241BenzeneSolvent

Procedure

In a round-bottom flask equipped with a Dean-Starke trap, 15.6 g of methyl 4-oxocyclohexanecarboxylate, 0.1 mol), morpholine (9.63 mL, 0.11 mol) and p-toluenesulfonic acid (5 mg) in benzene (42.3 mL) was heated up to reflux. Water was removed and the reaction was continued at reflux for 8 hours. The reaction mixture was then cooled to room temperature and concentrated in vacuo to give crude product as a yellow oil (20 g), which was used for next step without further purification.

Workup

  1. temperaturewas heated up
  2. temperatureto reflux
  3. customWater was removed
  4. temperatureat reflux for 8 hours
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d7923f85201b4c76a45268f20367c100
Source dataset
uspto-grants-2016_01
Patent number
US09242981B2

Linked notes

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