Reaktion #1800989

ord-7a19876f3bec496f9f0047c810dc5e80

Reaktionsgleichung

C[C@@H]1CN(c2ccc([N+](=O)[O-])cc2)C[C@H](C)O1
cis-2,6-dimethyl-4-(4-nitrophenyl)morpholine
C[C@@H]1CN(c2ccc([N+](=O)[O-])cc2)C[C@H](C)O1
Intermediate 68
C[C@@H]1CN(c2ccc([N+](=O)[O-])cc2)C[C@H](C)O1
cis-2,6-dimethyl-4-(4-nitrophenyl)morpholine
→
C[C@@H]1CN(c2ccc(N)cc2)C[C@H](C)O1
title compound
Ausbeute 100.0%
C[C@@H]1CN(c2ccc(N)cc2)C[C@H](C)O1
4-[cis-2,6-dimethylmorpholin-4-yl]aniline
Ausbeute 100.0%

Edukte

C[C@@H]1CN(c2ccc([N+](=O)[O-])cc2)C[C@H](C)O1
cis-2,6-dimethyl-4-(4-nitrophenyl)morpholine
C[C@@H]1CN(c2ccc([N+](=O)[O-])cc2)C[C@H](C)O1
Intermediate 68
C[C@@H]1CN(c2ccc([N+](=O)[O-])cc2)C[C@H](C)O1
cis-2,6-dimethyl-4-(4-nitrophenyl)morpholine

Reagenzien

[Pd]
palladium on carbon

Lösungsmittel

CCO
ethanol

Reaktionsbedingungen

Temperatur
50°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    FiltrationThe mixture was filtered
  2. 2
    Einengenthe filtrate was concentrated by evaporation

Vorschrift

A mixture of cis-2,6-dimethyl-4-(4-nitrophenyl)morpholine (Intermediate 68, 8.0 g) and 10% palladium on carbon (800 mg) in ethanol (100 mL) was stirred under an atmosphere of hydrogen at 50° C. for 6 h. The mixture was filtered and the filtrate was concentrated by evaporation to give the title compound (4.3 g, 100%) as an oil which subsequently solidified; 1H NMR δ (CDCl3): 6.79 (2H, d), 6.65 (2H, d), 3.81 (2H, m), 3.25 (2H, d), 2.33, (2H, t), 1.23 (6H, d); MS m/e MH+: 207.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07795283B2uspto-grants-2010_09