Trifluoroacetic acid → 1-[3-(Methyloxy)-4-nitrophenyl]-4-(4-piperidinyl)piperazine

HRID 419394Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 419394
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:17][CH2:16][N:15]([CH:18]3[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19]3)[CH2:14][CH2:13]2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:13][CH2:14][N:15]([CH:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)[CH2:16][CH2:17]2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 594526201,1-Dimethylethyl 4-{4-[3-(methyloxy)-4-nitrophenyl]-1-piperazinyl}-1-piperidinecarboxylate

Produkt 1

HCID 594529341-[3-(Methyloxy)-4-nitrophenyl]-4-(4-piperidinyl)piperazineAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 1,1-dimethylethyl 4-{4-[3-(methyloxy)-4-nitrophenyl]-1-piperazinyl}-1-piperidinecarboxylate (5.67 g, 13.5 mmol) and DCM (110 mL) was cooled with an ice/H2O bath. TFA (30.0 mL, 389 mmol) was added dropwise via addition funnel. Upon completion, by TLC, the reaction mixture was quenched with 1N NaOH (300 mL), extracted with DCM, dried (MgSO4) and concentrated to provide the title compound of step D (4.01 g, 12.5 mmol, 93%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.20-1.31 (m, 2H), 1.68 (d, J=9.9 Hz, 2H), 2.22-2.32 (m, 2H), 2.34-2.45 (m, 2H), 2.54-2.61 (m, 4H), 2.95 (d, J=12.1 Hz, 2H), 3.36-3.43 (m, 4H), 3.88 (s, 3H), 6.50 (d, J=2.6 Hz, 1H), 6.57 (dd, J=9.4, 2.4 Hz, 1H), 7.86 (d, J=9.5 Hz, 1H).

Aufarbeitung

  1. customUpon completion, by TLC, the reaction mixture was quenched with 1N NaOH (300 mL)
  2. extractionextracted with DCM
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-170112aed4384c3cb920dde85df108f1
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093239B2

Notizen zur Reaktion

Wird geladen…