Triethylamine → Methyl 4-(3-(1-acetylpiperazin-4-yl)anilino)-3-nitrobenzoate

HRID 49820

反応式

HRID 49820 の反応式
Cl[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[C:15]([N:18]1[CH2:23][CH2:22][N:21]([C:24]2[CH:25]=[C:26]([CH:28]=[CH:29][CH:30]=2)[NH2:27])[CH2:20][CH2:19]1)(=[O:17])[CH3:16].C(N(CC)CC)C>CN1C(=O)CCC1>[C:15]([N:18]1[CH2:19][CH2:20][N:21]([C:24]2[CH:25]=[C:26]([CH:28]=[CH:29][CH:30]=2)[NH:27][C:2]2[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=2[N+:12]([O-:14])=[O:13])[CH2:22][CH2:23]1)(=[O:17])[CH3:16]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 735797Methyl 4-chloro-3-nitrobenzoateHCID 111175391-[4-(3-Aminophenyl)piperazin-1-yl]ethan-1-one

生成物 1

HCID 22741905Methyl 4-(3-(1-acetylpiperazin-4-yl)anilino)-3-nitrobenzoate収率 85%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
80 °C

実験手順

To a solution of methyl 4-chloro-3-nitrobenzoate (2.0 g, 9.28 mmol) in anhydrous NMP (5 ml) was added 2d (2.03 g, 9.28 mmol) and triethylamine (1.3 ml, 9.28 mmol). The mixture was heated with stirring to 80° C. overnight. The cooled solution was poured into ice-water (50 ml) and the resulting mixture was extracted with ethyl acetate (3×10 ml). The combined organic extracts were washed with water, dried over sodium sulfate and evaporated to dryness. The residue was triturated with petroleum ether to yield methyl 4-(3-(1-acetylpiperazin-4-yl)anilino)-3-nitrobenzoate (3.14 g, 85%) as red crystals.

後処理

  1. temperatureThe mixture was heated
  2. extractionthe resulting mixture was extracted with ethyl acetate (3×10 ml)
  3. washThe combined organic extracts were washed with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated to dryness
  6. customThe residue was triturated with petroleum ether

出典と根拠

ORDレコード
ord-d28c7b02f5b34d5cb4e0639f13bf4dc5
出典データセット
uspto-grants-2004_03
特許番号
US06710044B2

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