4-Methoxybenzaldehyde → HCID 16117296, 화합물

HRID 1012581노트

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HRID 1012581 반응식
[CH2:1]([N:4]([CH2:19][CH2:20][CH3:21])[CH2:5][CH2:6][CH2:7][CH2:8][NH:9][CH2:10][C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=1)[CH2:2][CH3:3].[CH3:22][O:23][C:24]1[CH:31]=[CH:30][C:27]([CH:28]=O)=[CH:26][CH:25]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C(O)C>[CH2:19]([N:4]([CH2:1][CH2:2][CH3:3])[CH2:5][CH2:6][CH2:7][CH2:8][N:9]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([C:15]#[N:16])=[CH:17][CH:18]=1)[CH2:28][C:27]1[CH:30]=[CH:31][C:24]([O:23][CH3:22])=[CH:25][CH:26]=1)[CH2:20][CH3:21]

참가 물질

6

반응물 4

HCID 312444-MethoxybenzaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 15965417HCID 15965417, 화합물

생성물 1

HCID 16117296HCID 16117296, 화합물수율 69.3%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
0 °C

실험 절차

0.570 g (1.98 mmol) of 4-[(4-dipropylaminobutyl)amino]methylbenzonitrile (2a), 11.4 ml of ethanol, and 0.540 g (3.97 mmol, 2.0 equivalents) of 4-methoxybenzaldehyde were charged in a 50 ml recovery flask under a nitrogen stream. The mixture was then cooled to 0° C. After the addition of 1.009 g (4.76 mmol, 2.4 equivalents) of sodium triacetoxyborohydride, the mixture was stirred at room temperature for 18 hours. After confirming the disappearance of the raw material by TLC, the reaction solution was added to 50 ml of a saturated sodium bicarbonate aqueous solution, and extracted twice with 50 ml of chloroform. The chloroform layer was washed with 100 ml of a saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate, concentrated, and purified by silica gel column chromatography (Chromatorex NH, chloroform:n-hexane=1:1), thereby obtaining 0.559 g of 4-{[(4-dipropylaminobutyl)-(4-methoxybenzyl)amino]-methyl}-benzonitrile (19) as a light yellow oily substance (yield: 69.2%). [HPLC: 99.4% (HPLC measurement conditions B)]

후처리

  1. extractionextracted twice with 50 ml of chloroform
  2. washThe chloroform layer was washed with 100 ml of a saturated sodium chloride aqueous solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. custompurified by silica gel column chromatography (Chromatorex NH, chloroform:n-hexane=1:1)

출처 및 근거

ORD 기록
ord-6286eb902818486a92253559b5390198
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07977512B2

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