Benzenamine, 3-bromo-4-methyl- → N-(3-bromo-4-methyl-phenyl)4-(4-methyl-piperazin-1-ylmethyl)-benzamide

HRID 273289

反応式

HRID 273289 の反応式
C[Al](C)C.[Br:5][C:6]1[CH:7]=[C:8]([CH:10]=[CH:11][C:12]=1[CH3:13])[NH2:9].C[O:15][C:16](=O)[C:17]1[CH:22]=[CH:21][C:20]([CH2:23][N:24]2[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]2)=[CH:19][CH:18]=1>C1(C)C=CC=CC=1>[CH3:13][C:12]1[CH:11]=[CH:10][C:8]([NH:9][C:16](=[O:15])[C:17]2[CH:18]=[CH:19][C:20]([CH2:23][N:24]3[CH2:25][CH2:26][N:27]([CH3:30])[CH2:28][CH2:29]3)=[CH:21][CH:22]=2)=[CH:7][C:6]=1[Br:5]

参加物

5

反応物 3

HCID 82187Benzenamine, 3-bromo-4-methyl-HCID 782222Methyl 4-((4-methylpiperazin-1-yl)methyl)benzoateHCID 16682925Trimethylaluminum

生成物 1

HCID 10309714N-(3-bromo-4-methyl-phenyl)4-(4-methyl-piperazin-1-ylmethyl)-benzamide

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
0 °C

実験手順

A solution of trimethylaluminium (2M in toluene, 15.0 ml) is added over a period of 30 min to a solution of 3-bromo-4-methyl-aniline(2.15 g, 11.5 mmol) and 4-(4-methyl-piperazin-1-ylmethyl)-benzoic acid methyl ester (2.87 g, 11.5 mmol) in toluene (20 ml) at 40° C. under an atmosphere of argon. After gas evolution ceases, the reaction mixture is stirred 30 min before being cooled to 0° C. and partitioned between cold aqueous 1N NaOH (100 ml) and toluene (100 ml). The organic layer is extracted with aqueous saturated NH4Cl (100 ml) and aqueous saturated NaCl (100 ml) The organic layer is concentrated in vacuo to give 4.69 g (97 area % by HPLC) of the title compound as pale yellow crystals.

後処理

  1. custompartitioned between cold aqueous 1N NaOH (100 ml) and toluene (100 ml)
  2. extractionThe organic layer is extracted with aqueous saturated NH4Cl (100 ml) and aqueous saturated NaCl (100 ml) The organic layer
  3. concentrationis concentrated in vacuo

出典と根拠

ORDレコード
ord-a96d00eed30545c5bcbe3c64f9b42c98
出典データセット
uspto-grants-2008_11
特許番号
US07456283B2

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