Acetic Anhydride → 1-Acetyl-4-{1-[3-(methyloxy)-4-nitrophenyl]-4-piperidinyl}piperazine

HRID 419372Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 419372
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:17][CH2:16][CH:15]([N:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)[CH2:14][CH2:13]2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10].[CH3:24][C:25](OC(C)=O)=[O:26]>C(Cl)Cl>[C:25]([N:21]1[CH2:20][CH2:19][N:18]([CH:15]2[CH2:14][CH2:13][N:12]([C:5]3[CH:6]=[CH:7][C:8]([N+:9]([O-:11])=[O:10])=[C:3]([O:2][CH3:1])[CH:4]=3)[CH2:17][CH2:16]2)[CH2:23][CH2:22]1)(=[O:26])[CH3:24]

Komponenten

4

Edukt 2

HCID 7918Acetic AnhydrideHCID 598602641-{1-[3-(Methyloxy)-4-nitrophenyl]-4-piperidinyl}piperazine

Produkt 1

HCID 574161491-Acetyl-4-{1-[3-(methyloxy)-4-nitrophenyl]-4-piperidinyl}piperazineAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 1-{1-[3-(methyloxy)-4-nitrophenyl]-4-piperidinyl}piperazine (Example 57, step C) (0.500 g, 1.56 mmol) in DCM (20 mL) was added Ac2O (0.22 mL, 2.34 mmol). TEA (0.33 mL, 2.34 mmol) was then added dropwise and the resultant mixture was stirred at rt overnight. TLC indicated that the reaction had gone to completion. The reaction mixture was evaporated onto silica gel and purified by flash chromatography to afford the title compound of step A (0.52 g, 93%). 1H NMR (400 MHz, DMSO-d6) δ 7.85 (d, J=9.6 Hz, 1H), 6.57 (dd, J=9.5, 2.5 Hz, 1H), 6.48 (d, J=2.6 Hz, 1H), 4.07-4.00 (m, 2H), 3.88 (s, 3H), 3.41-3.34 (m, 4H), 2.99-2.89 (m, 2H), 2.43-2.36 (m, 2H), 1.95 (s, 3H), 1.85-1.78 (m, 2H), 1.48-1.38 (m, 2H).

Aufarbeitung

  1. customThe reaction mixture was evaporated onto silica gel
  2. custompurified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-22405836d06b4542bebdb4398d5f33c1
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093239B2

Notizen zur Reaktion

Wird geladen…