Norchlorcyclizine → Cetirizine ethyl ester

HRID 1871008Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1871008
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1.Cl[CH2:22][CH2:23][O:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27]>C(N(CC)CC)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:9]2[CH2:10][CH2:11][N:12]([CH2:22][CH2:23][O:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:13][CH2:14]2)=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 9340NorchlorcyclizineHCID 10964894Ethyl 2-(2-chloroethoxy)acetate

Produkt 1

HCID 9844843Cetirizine ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
135 °C

Versuchsvorschrift

10 gr. (0.035 mole) of 1-[(4-chlorophenyl)phenylmethyl]piperazine, 8.8 gr. (0.0525 mole) of ethyl 2-chloroethoxyacetate and 50 ml. of triethylamine were introduced into a pressure vessel. The mixture was stirred at 135° C. for 10 hours. It was cooled to 20° C. and filtered. The filtrate was evaporated and then distilled at 10 mbar pressure in order to remove the excess of the unreacted ethyl 2-chloroethoxyacetate. The oily residue obtained is sufficiently pure for the preparation of cetrizine by hydrolysis. The residue was purified over a silica gel chromatographic column. 13 gr. of ethyl [2-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]acetate is obtained as dark red oil (89.4% yield).

Aufarbeitung

  1. temperatureIt was cooled to 20° C.
  2. filtrationfiltered
  3. customThe filtrate was evaporated
  4. distillationdistilled at 10 mbar pressure in order
  5. customto remove the excess of the unreacted ethyl 2-chloroethoxyacetate
  6. customThe oily residue obtained
  7. customis sufficiently pure for the preparation of cetrizine by hydrolysis
  8. customThe residue was purified over a silica gel chromatographic column

Quellen und Nachweise

ORD-Eintrag
ord-f309c636952448d1ae25ac1045fc62c3
Quelldatensatz
uspto-grants-2000_08
Patentnummer
US06100400

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