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

HRID 1428546Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1428546
[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]

Komponenten

3

Edukt 1

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

Produkt 1

HCID 591345644-((4-Ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)anilineAusbeute 69,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-2b82600c23eb4c9d9fe15a578eeedf97
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08937071B2

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