Hydrochloric Acid → 2-Nitroimipramine

HRID 977046

Reaktionsgleichung

Reaktionsgleichung von HRID 977046
[CH3:1][N:2]([CH2:4][CH2:5][CH2:6][N:7]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[CH2:15][CH2:14][C:13]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]1=2)[CH3:3].[N+:22]([O-])([OH:24])=[O:23].Cl>C(O)(=O)C>[CH3:1][N:2]([CH2:4][CH2:5][CH2:6][N:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:14][CH2:15][C:16]2[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:17]1=2)[CH3:3]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 944Nitric AcidHCID 3696Imipramine

Produkt 1

HCID 1960452-NitroimipramineAusbeute 51,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel2×

Reaktionsbedingungen

Temperatur
18 °C

Versuchsvorschrift

Imipramine (26a, 1.925 g, 6.87 mmol) was dissolved in 32 mL acetic acid and cooled to 18° C., Conc. nitric acid (0.79 mL, 13 mmol) in 1.1 mL acetic acid was added dropwise, with stirring, keeping reaction at 17°-18° C., then reaction stirred at that temperature for an additional 20 minutes. The reaction was then poured into 130 mL of 0.15M HCl and washed with Et2O (2×85 mL), then pH adjusted to 13 with conc. NaOH and extracted with CHCl3 (4×100 mL). The CHCl3 extracts were combined, washed with 85 mL brine, dried over Na2SO4, and solvent removed in vacuo. The residue was purified by column chromatography, eluting with THF/Hex/NH4OH (70/30/0.4) to yield 1.145 g (51%) of the desired 2-nitroimipramine (26b) as a red oil. 1H NMR (200 MHz, CDCl3)d 8.0-7.9 (m, 2H), 7.3-7.0 (m, 5H), 3.9 (t, 2H), 3.2 (s, 4H), 2.3 (t, 2H), 2.1 (s, 6H), 1.7 (p, 2H); mass spec (FAB) (M+H)+ 326.

Aufarbeitung

  1. customreaction at 17°-18° C.
  2. customreaction
  3. stirringstirred at that temperature for an additional 20 minutes
  4. washwashed with Et2O (2×85 mL)
  5. extractionextracted with CHCl3 (4×100 mL)
  6. washwashed with 85 mL brine
  7. dry with materialdried over Na2SO4, and solvent
  8. customremoved in vacuo
  9. customThe residue was purified by column chromatography
  10. washeluting with THF/Hex/NH4OH (70/30/0.4)

Quellen und Nachweise

ORD-Eintrag
ord-e73980ad98754f43ae58f46b3b120f8c
Quelldatensatz
uspto-grants-1997_03
Patentnummer
US05614419

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