(4-Amino-2-(trifluoromethyl)phenyl)(4-ethylpiperazin-1-yl)methanone → 4-((4-Ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)aniline

HRID 1428546ノート

反応式

HRID 1428546 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH3:17])[CH2:12][CH2:11]2)=O)=[C:4]([C:18]([F:21])([F:20])[F:19])[CH:3]=1>C1COCC1>[CH2:16]([N:13]1[CH2:14][CH2:15][N:10]([CH2:8][C:5]2[CH:6]=[CH:7][C:2]([NH2:1])=[CH:3][C:4]=2[C:18]([F:21])([F:19])[F:20])[CH2:11][CH2:12]1)[CH3:17]

参加物

3

反応物 1

HCID 90417522(4-Amino-2-(trifluoromethyl)phenyl)(4-ethylpiperazin-1-yl)methanone

生成物 1

HCID 591345644-((4-Ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)aniline収率 69.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
80 °C

実験手順

To a mixture of (4-amino-2-trifluoromethyl-phenyl)-(4-ethyl-piperazin-1-yl)-methanone (20 g, 66.4 mmol) in THF (500 mL) was added BH3DMS (19.91 mL, 199 mmol) dropwise. Then the mixture was stirred at 80° C. for 4 h. The mixture was quenched by adding MeOH and then concentrated. The residue was purified by silica column chromatography on silica gel (PE:EA=2:1, Rf=0.35) to give a white solid of 4-(4-ethyl-piperazin-1-ylmethyl)-3-trifluoromethyl-phenylamine (14 g, 46.0 mmol, 69.4% yield): 1H NMR (400 MHz, CDCl3) δ: 7.48 (d, J=8.4 Hz, 1H), 6.91 (d, J=2.8 Hz, 1H), 6.79 (dd, J=2.4, 8.4 Hz, 1H), 3.76 (s, 2H), 3.53 (s, 2H), 2.45-2.39 (m, 8H), 1.08 (t, J=7.2 Hz, 3H); ES-LCMS m/z 288 (M+H).

後処理

  1. additionwas added BH3DMS (19.91 mL, 199 mmol) dropwise
  2. customThe mixture was quenched
  3. additionby adding MeOH
  4. concentrationconcentrated
  5. customThe residue was purified by silica column chromatography on silica gel (PE:EA=2:1, Rf=0.35)

出典と根拠

ORDレコード
ord-2b82600c23eb4c9d9fe15a578eeedf97
出典データセット
uspto-grants-2015_01
特許番号
US08937071B2

反応ノート

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