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

HRID 446617노트

반응식

HRID 446617 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-22089b6c563d47d2af3c37e4d914b872
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08476253B2

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