Cyclohexanone → HCID 71238639, compound

HRID 926023Notes

Reaction equation

HRID 926023 reaction equation
[C:1]([CH2:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][C:15]2[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:16]=2)=[CH:9][CH:8]=1)=[O:5])#[N:2].[C:25]1(=O)[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1.N1CCOCC1>C1(C)C=CC=CC=1>[C:1]([C:3](=[C:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1)[C:4]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:23][CH:24]=2)=[CH:11][CH:12]=1)=[O:5])#[N:2]

Participants

5

Reactant 3

HCID 7967CyclohexanoneHCID 8083MorpholineHCID 71238765HCID 71238765, compound

Product 1

HCID 71238639HCID 71238639, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

To a mixture of 54.0 g of methyl 4-(2-{4-[(cyanoacetyl)amino]phenyl}ethyl)benzoate, 50.0 mL of cyclohexanone, and 300 mL of toluene was added dropwise 15.0 mL of morpholine at room temperature. In a reaction apparatus to which a Dean-Stark type dehydration tube was attached, the reaction mixture was stirred at 120° C. for 3 hours. Subsequently, the reaction mixture was further heated to reflux and stirred for 1 hour. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure. To the residue was further added 200 mL of diisopropyl ether, followed by stirring for 14 hours. The precipitated solid was collected by filtration to obtain 53.2 g of methyl 4-[2-(4-{[cyano(cyclohexylidene)acetyl]amino}phenyl)ethyl]benzoate as a beige solid. ESI+: 403

Workup

  1. temperatureSubsequently, the reaction mixture was further heated
  2. temperatureto reflux
  3. stirringstirred for 1 hour
  4. temperatureThe reaction mixture was cooled to room temperature
  5. concentrationconcentrated under reduced pressure
  6. stirringby stirring for 14 hours
  7. filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-4e454f7579664b498137bc3cc82ae8d1
Source dataset
uspto-grants-2016_03
Patent number
US09284295B2

Reaction notes

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