4,4-Diaminodiphenylmethane → HCID 18465586, compound

HRID 2110554Notes

Reaction equation

HRID 2110554 reaction equation
[CH:1]1[C:6]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)=[CH:5][CH:4]=[C:3]([NH2:15])[CH:2]=1.[C:16]1(=O)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.[BH4-].[Na+].[OH-].[K+]>CO.C1(C)C=CC=CC=1>[CH:16]1([NH:15][C:3]2[CH:2]=[CH:1][C:6]([CH2:7][C:8]3[CH:13]=[CH:12][C:11]([NH:14][CH:1]4[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]4)=[CH:10][CH:9]=3)=[CH:5][CH:4]=2)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

7

Reactant 4

HCID 75774,4-DiaminodiphenylmethaneHCID 7967CyclohexanoneHCID 14797Potassium HydroxideHCID 4311764Sodium borohydride

Product 1

HCID 18465586HCID 18465586, compoundYield 102.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

30 ml of toluene was added to 4.000 g (20.175 mmol) of 4,4-methylenedianiline, 15.839 g (161.396 mmol) of cyclohexanone, and 10.0 g of molecular sieves (4 Å). The mixture was reacted at 100° C. for 2 days. The mixture was cooled to room temperature, molecular sieves were filtered, and dried in a vacuum at 60° C. to prepare 4-(4-(cyclohexylideneamino)benzyl)-N-cyclohexylidenebenzeneamine. The obtained product was dissolved in 60 ml of methanol, 4.576 g (121.047 mmol) of sodium borohydride was added thereto, and the mixture was reacted at room temperature for 2 hours. Then, the mixture was neutralized with 80 ml of 1 N KOH. An aqueous layer was extracted twice with 60 ml of M.C, and dried with MgSO4. Then, the obtained product was recrystallized in hexane and ethylacetate. As a result, 3.765 g of white solid product (Compound 1) was obtained (Yield: 51%).

Workup

  1. customThe mixture was reacted at 100° C. for 2 days
  2. filtrationmolecular sieves were filtered
  3. customdried in a vacuum at 60° C.
  4. customto prepare 4-(4-(cyclohexylideneamino)benzyl)-N-cyclohexylidenebenzeneamine
  5. customthe mixture was reacted at room temperature for 2 hours
  6. extractionAn aqueous layer was extracted twice with 60 ml of M.C
  7. dry with materialdried with MgSO4
  8. customThen, the obtained product was recrystallized in hexane

Sources & evidence

ORD record
ord-1b4854039a734f48ae998f7dc9380c38
Source dataset
uspto-grants-2009_04
Patent number
US07517940B2

Reaction notes

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