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Formic Acid → 3-(4-Isopropylpiperazin-1-yl)-5-(trifluoromethoxy)benzaldehyde

HRID 922384
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 922384
[O:1]1CCO[CH:2]1[C:6]1[CH:7]=[C:8]([N:17]2[CH2:22][CH2:21][N:20]([CH:23]([CH3:25])[CH3:24])[CH2:19][CH2:18]2)[CH:9]=[C:10]([O:12][C:13]([F:16])([F:15])[F:14])[CH:11]=1.C(O)=O>O>[CH:23]([N:20]1[CH2:19][CH2:18][N:17]([C:8]2[CH:7]=[C:6]([CH:11]=[C:10]([O:12][C:13]([F:16])([F:15])[F:14])[CH:9]=2)[CH:2]=[O:1])[CH2:22][CH2:21]1)([CH3:25])[CH3:24]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 284Formic AcidHCID 867193491-(3-(1,3-Dioxolan-2-yl)-5-(trifluoromethoxy)phenyl)-4-isopropylpiperazine

Produkt 1

HCID 867193503-(4-Isopropylpiperazin-1-yl)-5-(trifluoromethoxy)benzaldehydeAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Water (1.3 mL) was added to a suspension of 1-(3-(1,3-dioxolan-2-yl)-5-(trifluoromethoxy)phenyl)-4-isopropylpiperazine (22, 996 mg, 2.76 mmol) and formic acid (6.71 g, 145 mmol). The mixture was heated to 60° C. for 20 h. The reaction mixture was concentrated to a brown oil in vacuo. The oil was dissolved in EtOAc (100 mL) and the solution was washed with saturated aq. NaHCO3 solution (100 mL) and brine (100 mL). After drying over Na2SO4, the suspension was filtered and the filtrate concentrated to an orange oil. The residue was purified by silica gel chromatography eluting with 0-80% EtOAc in hexanes to afford the title compound (608 mg, 70%) as an orange oil: 1H NMR (500 MHz, CDCl3) δ 9.92 (s, 1H), 6.93 (s, 1H), 7.31 (s, 1H), 7.13 (s, 1H), 6.92 (s, 1H), 3.30-3.28 (m, 4H), 2.73 (sept, 1H), 2.70-2.64 (m, 4H), 1.10 (d, J=6.5 Hz, 6H).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated to a brown oil in vacuo
  2. dissolutionThe oil was dissolved in EtOAc (100 mL)
  3. washthe solution was washed with saturated aq. NaHCO3 solution (100 mL) and brine (100 mL)
  4. dry with materialAfter drying over Na2SO4
  5. filtrationthe suspension was filtered
  6. concentrationthe filtrate concentrated to an orange oil
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with 0-80% EtOAc in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-f6dc69c64e854e078db59df9fa20fc04
Quelldatensatz
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09278940B2

Notizen zur Reaktion

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