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

HRID 1428546노트

반응식

HRID 1428546 반응식
[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]

참가 물질

3

반응물 1

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
80 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-2b82600c23eb4c9d9fe15a578eeedf97
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08937071B2

반응 노트

불러오는 중…