Hydrochloric Acid → 2-Nitroimipramine

HRID 1654437

Reaktionsgleichung

Reaktionsgleichung von HRID 1654437
[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-2a4c08a66b534d26a71d65eea2dbae2c
Quelldatensatz
uspto-grants-1995_04
Patentnummer
US05407835

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