Benzophenone imine → Methyl 3-(diphenylmethyleneamino)cyclohexanecarboxylate

HRID 530872Notes

Reaction equation

HRID 530872 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH:4]([C:8]([O:10][CH3:11])=[O:9])[CH2:3]1.[C:12](=N)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>ClCCl>[C:13]1([C:12](=[N:1][CH:2]2[CH2:7][CH2:6][CH2:5][CH:4]([C:8]([O:10][CH3:11])=[O:9])[CH2:3]2)[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 136809Benzophenone imineHCID 13216966Methyl 3-aminocyclohexane-1-carboxylate

Product 1

HCID 86698247Methyl 3-(diphenylmethyleneamino)cyclohexanecarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a flask, methyl 3-aminocyclohexanecarboxylate (3.86 g, 19.94 mmol) was dissolved in dichloromethane (80 mL). Benzophenone imine (3.33 mL, 19.94 mmol) was added to the reaction, and the reaction was stirred at room temperature for 24 hrs. Upon completion, the reaction was concentrated and triturated with diethyl ether. The suspension was filtered. This trituration process was done twice. The remaining filtrate was concentrated and progressed to the next step without further purification.

Workup

  1. concentrationUpon completion, the reaction was concentrated
  2. customtriturated with diethyl ether
  3. filtrationThe suspension was filtered
  4. concentrationThe remaining filtrate was concentrated
  5. customprogressed to the next step without further purification

Sources & evidence

ORD record
ord-2d8b0faaa1744303bd7cbe87e74a3fe9
Source dataset
uspto-grants-2016_05
Patent number
US09351965B2

Reaction notes

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