4-Aminobenzaldehyde → 2-(4-Amino-benzylidene)-6-isopropyl-3-methyl-cyclohexanone

HRID 1246007

Reaction equation

HRID 1246007 reaction equation
[CH:1]([CH:4]1[C:9](=[O:10])[C:8](=[CH:11][C:12]2[CH:17]=[CH:16][C:15]([N:18]=CC3C=CC(OCCC)=CC=3)=[CH:14][CH:13]=2)[CH:7]([CH3:30])[CH2:6][CH2:5]1)([CH3:3])[CH3:2].C[C@H]1CC(=O)[C@H](C(C)C)CC1.NC1C=CC(C=O)=CC=1.[OH-].[K+]>CS(C)=O.O.C(OCC)(=O)C>[NH2:18][C:15]1[CH:14]=[CH:13][C:12]([CH:11]=[C:8]2[CH:7]([CH3:30])[CH2:6][CH2:5][CH:4]([CH:1]([CH3:2])[CH3:3])[C:9]2=[O:10])=[CH:17][CH:16]=1

Participants

8

Reactant 4

HCID 111584-AminobenzaldehydeHCID 14797Potassium HydroxideHCID 26447MenthoneHCID 28510996-Isopropyl-3-methyl-2-{4-[(4-propoxy-benzylidene)-amino]-benzylidene}-cyclohexanone3×

Product 1

HCID 50230232-(4-Amino-benzylidene)-6-isopropyl-3-methyl-cyclohexanone

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A compound having general Formula 3, exemplified by 6-Isopropyl-3-methyl-2-{4-[(4-propoxy-benzylidene)-amino]-benzylidene}-cyclohexanone (Compound 3; FIG. 1) can be prepared as follows. A solution of menthone (154 mg, 1.0 mmol) and 4-aminobenzaldehyde (121 mg, 1.0 mmol) in dimethylsulfoxide is treated with potassium hydroxide (56 mg, 1.0 mmol). The reaction is stirred until no further reaction occurs. The reaction mixture is poured into ethyl acetate and water. The organic phase is collected, dried and concentrated to give 2-(4-Amino-benzylidene)-6-isopropyl-3-methyl-cyclohexanone. The 2-(4-Amino-benzylidene)-6-isopropyl-3-methyl-cyclohexanone is dissolved in dichloromethane and treated with 4-propoxybenzaldehyde (164 mg, 1.0 mmol) and anhydrous Na2SO4. The reaction mixture is stirred until no further reaction occurs. The reaction mixture is filtered and concentrated to give the title compound.

Workup

  1. customcan be prepared
  2. customThe organic phase is collected
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a31e71f513f145ae8fcdc7ebee109738
Source dataset
uspto-grants-2006_10
Patent number
US07125908B2

Linked notes

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