Water → 4,4',4''-Methanetriyltris(N-methylaniline)

HRID 2180864Notes

Reaction equation

HRID 2180864 reaction equation
[CH:1]([NH:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([C:20]2[CH:25]=[CH:24][C:23]([NH:26][CH:27]=O)=[CH:22][CH:21]=2)[C:11]2[CH:16]=[CH:15][C:14]([NH:17][CH:18]=O)=[CH:13][CH:12]=2)=[CH:6][CH:5]=1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[CH3:18][NH:17][C:14]1[CH:13]=[CH:12][C:11]([CH:10]([C:7]2[CH:6]=[CH:5][C:4]([NH:3][CH3:1])=[CH:9][CH:8]=2)[C:20]2[CH:25]=[CH:24][C:23]([NH:26][CH3:27])=[CH:22][CH:21]=2)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 22490733HCID 22490733, compound

Product 1

HCID 224905374,4',4''-Methanetriyltris(N-methylaniline)Yield 70.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The tris(4-formylaminophenyl)methane (130 mg) obtained in Reference Example 31 was dissolved in tetrahydrofuran (5 ml), after which lithium aluminum hydride (66.1 mg) was added under a nitrogen atmosphere at 5° C., the temperature was raised to room temperature, and the mixture was stirred for 19 hours. Water (5 ml) was added to the reaction mixture at 5° C., and stirring was continued for 10 minutes. The reaction mixture was filtered with celite and the filtrate was concentrated to dryness. The residue was purified by silica gel column chromatography (Kiesel-gel 60, 240-400 mesh) and elution was performed with a mixed solvent of chloroform:methanol=98:2 to obtain 81.1 mg of the title compound as a yellow oily substance (70% yield).

Workup

  1. stirringstirring
  2. waitwas continued for 10 minutes
  3. filtrationThe reaction mixture was filtered with celite
  4. concentrationthe filtrate was concentrated to dryness
  5. customThe residue was purified by silica gel column chromatography (Kiesel-gel 60, 240-400 mesh) and elution

Sources & evidence

ORD record
ord-9ab64185f5e3410992afef1cf9ea6d58
Source dataset
uspto-grants-2005_05
Patent number
US06887890B2

Reaction notes

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