Morpholine → Methyl 4-morpholinocyclohex-3-enecarboxylic acid

HRID 62450Notes

Reaction equation

HRID 62450 reaction equation
[CH3:1][C:2]1([C:9]([OH:11])=[O:10])[CH2:7][CH2:6][C:5](=O)[CH2:4][CH2:3]1.[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:1][C:2]1([C:9]([OH:11])=[O:10])[CH2:7][CH2:6][C:5]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:4][CH2:3]1

Participants

5

Reactant 2

HCID 8083MorpholineHCID 226099431-Methyl-4-oxocyclohexane-1-carboxylic acid

Product 1

HCID 71222953Methyl 4-morpholinocyclohex-3-enecarboxylic acidYield 103.3%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

The solution of methyl 4-oxocyclohexanecarboxylic acid (172.0 g, 1.01 mol), morpholine (97.0 g, 1.11 mol) and p-toluenesulfonic acid (200 mg) in toluene (500 mL) was stirred 18 h at reflux. The reaction mixture was concentrated in vacuum to give 235 g methyl 4-morpholinocyclohex-3-enecarboxylic acid. The compound was used in the next reaction without further purification.

Workup

  1. temperatureat reflux
  2. concentrationThe reaction mixture was concentrated in vacuum

Sources & evidence

ORD record
ord-742f57711c2543ef960c53012a8ae041
Source dataset
uspto-grants-2016_09
Patent number
US09446130B2

Reaction notes

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