Trifluoroacetic acid → 4-(4-Nitrophenoxy)piperidine

HRID 1403714Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1403714
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[N+:21]([C:18]1[CH:19]=[CH:20][C:15]([O:14][CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[CH:16][CH:17]=1)([O-:23])=[O:22]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 2794776Tert-butyl 4-(4-nitrophenoxy)piperidine-1-carboxylate

Produkt 1

HCID 219186534-(4-Nitrophenoxy)piperidineAusbeute 113,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 4-(4-nitro-phenoxy)-piperidine-1-carboxylic acid tert-butyl ester (10.0 g, 31.02 mmol) in DCM (50 mL) was treated with TFA (50 mL) and stirred at ambient temperature for 2 hours. The solvent was removed under vacuum, the residue basified with NH4OH and extracted into DCM (3×). The combined extracts were washed with brine, dried over Na2SO4 and concentrated under vacuum to afford the title compound (7.81 g, quantitative yield) as a yellow residue. 1H NMR (300 MHz, CDCl3) δ 8.18 (m, 2H), 6.94 (m, 2H), 4.52 (m, 1H), 3.18 (m, 2H), 2.79 (m, 2H), 2.38 (br s, 1H), 2.05 (m, 2H), 1.72 (m, 2H). LCMS (m/z, Method A) ES+ 223.1 [M+1]+.

Aufarbeitung

  1. customThe solvent was removed under vacuum
  2. extractionextracted into DCM (3×)
  3. washThe combined extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-fd0c684d2b334aee9558627c11c063e0
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08912219B2

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