Cyclohexanone → HCID 71238801, compound

HRID 926025Notes

Reaction equation

HRID 926025 reaction equation
[C:1]([CH2:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][C:16]2[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=2)=[CH:9][CH:8]=1)=[O:5])#[N:2].[C:26]1(=O)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1.N1CCOCC1>C1(C)C=CC=CC=1>[C:1]([C:3](=[C:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)[C:4]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:13][CH2:14][CH2:15][C:16]2[CH:17]=[CH:18][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:24][CH:25]=2)=[CH:11][CH:12]=1)=[O:5])#[N:2]

Participants

5

Reactant 3

HCID 7967CyclohexanoneHCID 8083MorpholineHCID 71238730HCID 71238730, compound

Product 1

HCID 71238801HCID 71238801, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of 19.3 g of methyl 4-(3-{4-[(cyanoacetyl)amino]phenyl}propyl)benzoate, 18 mL of cyclohexanone, and 100 mL of toluene was added dropwise 5.0 mL of morpholine at room temperature. In a reaction device in which a Dean-Stark type dehydration tube was installed, the reaction mixture was stirred for 8 hours under heating and refluxing. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane-chloroform and ethyl acetate-chloroform) to obtain methyl 4-[3-(4-{[cyano(cyclohexylidene)acetyl]amino}phenyl)propyl]benzoate in the form of a reddish brown amorphous substance as a crude product. ESI+:417

Workup

  1. temperatureunder heating
  2. temperaturerefluxing
  3. concentrationconcentrated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (n-hexane-chloroform and ethyl acetate-chloroform)

Sources & evidence

ORD record
ord-ed76841b34444ee683120b0867bfc459
Source dataset
uspto-grants-2016_03
Patent number
US09284295B2

Reaction notes

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