4-Methoxybenzaldehyde → HCID 16117296、化合物

HRID 1012581ノート

反応式

HRID 1012581 の反応式
[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]

参加物

6

反応物 4

HCID 312444-MethoxybenzaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 15965417HCID 15965417、化合物

生成物 1

HCID 16117296HCID 16117296、化合物収率 69.3%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
0 °C

実験手順

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)]

後処理

  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)

出典と根拠

ORDレコード
ord-6286eb902818486a92253559b5390198
出典データセット
uspto-grants-2011_07
特許番号
US07977512B2

反応ノート

読み込み中…