Methyl 4-(aminomethyl)benzoate hydrochloride → Benzyl methyl 4,4'-[iminobis(methylene)]dibenzoate

HRID 446617Notes

Reaction equation

HRID 446617 reaction equation
[CH:1]([C:3]1[CH:18]=[CH:17][C:6]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])=[CH:5][CH:4]=1)=O.Cl.[NH2:20][CH2:21][C:22]1[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][CH:23]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[NH:20]([CH2:21][C:22]1[CH:23]=[CH:24][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:30][CH:31]=1)[CH2:1][C:3]1[CH:18]=[CH:17][C:6]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 2729253Methyl 4-(aminomethyl)benzoate hydrochlorideHCID 5049666Sodium triacetoxyborohydrideHCID 11528845Benzyl 4-formylbenzoate

Product 1

HCID 66671564Benzyl methyl 4,4'-[iminobis(methylene)]dibenzoateYield 54%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Benzyl 4-formylbenzoate (618 mg, 2.57 mmol) and methyl 4-(aminomethyl)benzoate hydrochloride (622 mg, 3.09 mmol) were dissolved in 20 mL of toluene and 2.0 mL of methanol, and the solvent was evaporated under reduced pressure. The resulting white solid was dissolved in 15 mL of 2-propanol, sodium triacetoxyborohydride (1.64 g, 7.72 mmol) was added, and the mixture was stirred at room temperature for 5 hours. The reaction mixture was diluted with ethyl acetate and washed with a saturated aqueous sodium hydrogencarbonate solution and saturated sodium chloride solution. The organic layer was dried with anhydrous magnesium sulfate, then the solvent was evaporated under reduced pressure, and the resulting yellow oily substance was purified by silica gel chromatography (n-hexane:ethyl acetate, 90:10→80:20, v/v) to give the title compound (0.54 g; yield, 54%) as a white solid.

Workup

  1. custom2.0 mL of methanol, and the solvent was evaporated under reduced pressure
  2. dissolutionThe resulting white solid was dissolved in 15 mL of 2-propanol
  3. washwashed with a saturated aqueous sodium hydrogencarbonate solution and saturated sodium chloride solution
  4. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customthe resulting yellow oily substance was purified by silica gel chromatography (n-hexane

Sources & evidence

ORD record
ord-22089b6c563d47d2af3c37e4d914b872
Source dataset
uspto-grants-2013_07
Patent number
US08476253B2

Reaction notes

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