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Water → Tert-butyl 4-(3,5,6-trifluoropyridin-2-yl)piperazine-1-carboxylate

HRID 912806
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 912806
F[C:2]1[C:7]([F:8])=[CH:6][C:5]([F:9])=[C:4]([F:10])[N:3]=1.[C:11]([N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].C(N(CC)C(C)C)(C)C.O>CN1C(=O)CCC1>[C:14]([O:13][C:11]([N:18]1[CH2:23][CH2:22][N:21]([C:2]2[C:7]([F:8])=[CH:6][C:5]([F:9])=[C:4]([F:10])[N:3]=2)[CH2:20][CH2:19]1)=[O:12])([CH3:17])([CH3:15])[CH3:16]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 1377492,3,5,6-TetrafluoropyridineHCID 143452tert-Butyl piperazine-1-carboxylate

Produkt 1

HCID 67398573Tert-butyl 4-(3,5,6-trifluoropyridin-2-yl)piperazine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387
N-methyl-2-pyrrolidone
Lösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

A mixture of 2,3,5,6-tetrafluoropyridine (755 mg, 5 mmol, Aldrich), 1-Boc-piperazine (558 mg, 3 mmol, Aldrich) and N,N-diisopropylethylamine (1 mL, 5.8 mmol, Aldrich) in NMP (5 mL) was heated at 150° C. for 16 h. The reaction mixture was cooled to room temperature, water (25 mL) was added, and the mixture was extracted with EtOAc (2×40 mL). The combined organic phases were washed with brine (50 mL), then dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo and the residue was purified by silica gel column chromatography, eluting with 20% EtOAc/hexane to give the title compound as a white solid. MS (ESI, pos. ion) m/z: 318 (M+1).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionthe mixture was extracted with EtOAc (2×40 mL)
  3. washThe combined organic phases were washed with brine (50 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe residue was purified by silica gel column chromatography
  8. washeluting with 20% EtOAc/hexane

Quellen und Nachweise

ORD-Eintrag
ord-5ab938e5834b4b3a84a5e116648890d8
Quelldatensatz
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08026241B2

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