Reaktion #162657

ord-c1e22a7237c74b988d172c1343aeb4a4

Reaktionsgleichung

O=C1OCCO1
ethylene carbonate
O=C([O-])[O-].[K+].[K+]
potassium carbonate
CN(C)CCOc1ncccc1O
2-(2-Dimethylaminoethoxy)pyridin-3-ol
O=C1OCCO1
ethylene carbonate
CN(C)CCOc1ncccc1OCCO
title compound
CN(C)CCOc1ncccc1OCCO
2-{[2-(2-dimethylaminoethoxy)-3-pyridinyl]oxy}ethanol

Lösungsmittel

Reaktionsbedingungen

Temperatur
58°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.ADDITIONwas added through the manhood in portions

Vorschrift

DMSO (17 L) and potassium carbonate (8.2 kg) were charged to the 100 L-glasslined reactor. The mixture was heated to 58° C. while stirring. 2-(2-Dimethylaminoethoxy)pyridin-3-ol (4.11 kg) was charged to the reactor during 25 minutes (gas evolution). The mixture was heated to 117° C. before the prepared ethylene carbonate solution was added through the manhood in portions. After 1 L ethylene carbonate solution was added IP-HPLC was taken to ensure that the title compound had started to form. The total addition of ethylene carbonate solution was made during 1 h 35 minutes. Temperature after the addition was 124° C. A HPLC sample was taken from the reaction mixture 10 minutes after finished addition. It showed 95% conversion to product. The reaction-mixture was allowed to cool to 70° C. before water (45 L) and sodium chloride (4.06 kg) was charged to the reactor. The mixture was then stirred for 20 minutes at 70° C. before cooled to RT. Ethyl acetate (137 L) was charged into a 328 L glass-lined reactor. The water mixture was transferred from the 100 L reactor to the 328 L reactor. The mixture was stirred for 25 minutes before the mechanical stirrer was turned off. After allowing the phases to separate for 40 minutes, the water-phase (65 L) was discharged. The mixture was heated to reflux and 102 L of ethyl acetate was distilled off. Toluene (72 L) was added and the mixture was heated to reflux again and 61 L of toluene/ethyl acetate was distilled off. The reaction mixture was then cooled to RT. The title compound was never isolated; it was directly used in Example 2C.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08835439B2uspto-grants-2014_09