Hydrogen iodide → (Z)-2-Hydroxy Doxepin

HRID 1894780

Reaktionsgleichung

Reaktionsgleichung von HRID 1894780
C[O:2][C:3]1[CH:23]=[CH:22][C:6]2[O:7][CH2:8][C:9]3[CH:21]=[CH:20][CH:19]=[CH:18][C:10]=3[CH:11]([CH2:12][CH2:13][CH2:14][N:15]([CH3:17])[CH3:16])[C:5]=2[CH:4]=1.I>C(O)(=O)C>[OH:2][C:3]1[CH:23]=[CH:22][C:6]2[O:7][CH2:8][C:9]3[CH:21]=[CH:20][CH:19]=[CH:18][C:10]=3/[C:11](=[CH:12]/[CH2:13][CH2:14][N:15]([CH3:17])[CH3:16])/[C:5]=2[CH:4]=1

Komponenten

4

Edukt 2

HCID 24841Hydrogen iodideHCID 67320463Dibenz[b,e]oxepin-11-propanamine, 6,11-dihydro-2-methoxy-N,N-dimethyl-

Produkt 1

HCID 67319009(Z)-2-Hydroxy Doxepin

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 2-methoxy-11-(3-dimethylaminopropyl)-6,11-dihydrodibenzo[b,e]oxepin (165 mg, 0.005 mol) with glacial acetic acid (0.2 ml) and hydriodic acid (0.2 mL, 57%) was stirred and heated for 5 hr at 90° C. The product was then extracted and purified by pouring into ice water (25 mL), made alkaline with sodium hydroxide (2N) and extracted with ether (2×10 mL). The aqueous layer was then adjusted to pH 6.8 with hydrochloric acid (6N). The mixture was then brought to pH 7 by the addition of sodium bicarbonate solution (5%) and extracted with chloroform (2×10 mL). The extract was dried over anhydrous sodium sulfate and evaporated in vacuo to give a yellowish solid. The crude reaction product was purified by preparative TLC (chloroform/toluene/methanol/ammonia, 4:3:2:1, v/v).

Aufarbeitung

  1. extractionThe product was then extracted
  2. custompurified
  3. additionby pouring into ice water (25 mL)
  4. extractionextracted with ether (2×10 mL)
  5. additionThe mixture was then brought to pH 7 by the addition of sodium bicarbonate solution (5%)
  6. extractionextracted with chloroform (2×10 mL)
  7. dry with materialThe extract was dried over anhydrous sodium sulfate
  8. customevaporated in vacuo
  9. customto give a yellowish solid
  10. customThe crude reaction product
  11. customwas purified by preparative TLC (chloroform/toluene/methanol/ammonia, 4:3:2:1

Quellen und Nachweise

ORD-Eintrag
ord-30a6eefcbbd2497eb289a195b7199d12
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08513299B2

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