4-Nitrobenzyl bromide → HCID 19045334、化合物

HRID 1781384ノート

反応式

HRID 1781384 の反応式
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8]Br)=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:12]([NH:15][C:16]1[CH:17]=[CH:18][C:19]2[O:29][C:23]3([CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)[CH2:22][C:21](=[O:30])[C:20]=2[CH:31]=1)(=[O:14])[CH3:13].C(N(C(C)C)CC)(C)C.CO.C(Cl)(Cl)Cl>CN(C)C=O>[C:12]([NH:15][C:16]1[CH:17]=[CH:18][C:19]2[O:29][C:23]3([CH2:24][CH2:25][N:26]([CH2:8][C:7]4[CH:10]=[CH:11][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=4)[CH2:27][CH2:28]3)[CH2:22][C:21](=[O:30])[C:20]=2[CH:31]=1)(=[O:14])[CH3:13]

参加物

6

反応物 4

HCID 660114-Nitrobenzyl bromideHCID 81531DiisopropylethylamineHCID 19045273HCID 19045273、化合物HCID 21584188Chloroform methanol

生成物 1

HCID 19045334HCID 19045334、化合物収率 59.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of 4-nitrobenzyl bromide (0.73 g, 3.4 mmol), 3,4-dihydro-6-acetamidospiro[(2H)-benzopyran-2,4'-piperidine]-4-one (0.94 g, 3.4 mmol) and diisopropylethylamine (0.61 ml, 3.5 mmol) in dimethylformamide (15 ml) was stirred at room temperature for 3 hr. The reaction mixture was then concentrated under reduced pressure. The residue was diluted with methylene chloride and washed with saturated sodium bicarbonate solution, water and brine. Drying and solvent evaporation gave an oil; flash chromatography (silica gel, methanol-chloroform 2/98) gave 3,4-dihydro-6-acetamido-1'-(4-nitrobenzyl)spiro[(2H)-1-benzopyran-2,4'-piperidine]-4-one (0.83 g, 59%); 75 mg converted to hydrochloride; mp>250° C.

後処理

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. additionThe residue was diluted with methylene chloride
  3. washwashed with saturated sodium bicarbonate solution, water and brine
  4. customDrying
  5. customsolvent evaporation
  6. customgave an oil

出典と根拠

ORDレコード
ord-947d6841260549d3b54d67fb4a7179a9
出典データセット
uspto-grants-1997_05
特許番号
US05633247

反応ノート

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