1-Chloroethyl chloroformate → 7-methoxy-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride

HRID 228257Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 228257
[Cl:1][C:2]([O:4][CH:5](Cl)[CH3:6])=O.CO[CH:10]1[C:16]2[CH:17]=CC=[CH:20][C:15]=2[CH2:14][CH2:13][N:12](C)[CH2:11]1>ClCCCl>[ClH:1].[CH3:2][O:4][C:5]1[CH:6]=[CH:17][C:16]2[CH2:10][CH2:11][NH:12][CH2:13][CH2:14][C:15]=2[CH:20]=1

Komponenten

4

Edukt 2

HCID 5213051-Chloroethyl chloroformateHCID 68748342methoxy-3-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Produkt 1

HCID 212429067-methoxy-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochlorideAusbeute 179 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

The reactions are set up in a 22 L flask, each equipped with a mechanical stirrer, heating mantle, condenser and nitrogen bubbler. Add 1-chloroethyl chloroformate (620 mL, 5.750 mol, 10.0 eq) over 1 hour to methoxy-3-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine (110 g, 575 mmol, 1.0 eq) dissolved in 1,2-dichloroethane (8.0 L) at 60° C. under nitrogen, in a 22 L flask. The solution turns dark purple over the next 2 hours. Heat the mixture to reflux and stir for 16 hours under nitrogen. The reaction is determined to be complete by TLC. Cool the reaction flask and concentrate under vacuum to an oil. Dissolve the oil in methanol (4 L) and add to a 22 L reaction flask and stir for 16 hours at room temperature under nitrogen. Concentrate the resulting solution under vacuum to an off-white solid 220 g, 90% yield).

Aufarbeitung

  1. customThe reactions are set up in a 22 L flask
  2. customeach equipped with a mechanical stirrer
  3. temperatureheating mantle, condenser and nitrogen bubbler
  4. customturns dark purple over the next 2 hours
  5. temperatureHeat the mixture
  6. temperatureto reflux
  7. temperatureCool the reaction flask
  8. concentrationconcentrate under vacuum to an oil
  9. dissolutionDissolve the oil in methanol (4 L)
  10. additionadd to a 22 L reaction flask
  11. stirringstir for 16 hours at room temperature under nitrogen

Quellen und Nachweise

ORD-Eintrag
ord-8b109da5f09a4365b621655df9febaab
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560463B2

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