Triethylamine → 4-(2-Dimethylaminoethyl)-1-[2-(4-methylphenoxy)ethyl]piperidine dihydrochloride

HRID 962442Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 962442
[ClH:1].Cl.[CH3:3][N:4]([CH3:13])[CH2:5][CH2:6][CH:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1.[CH3:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23]Br)=[CH:17][CH:16]=1.C(N(CC)CC)C.[OH-].[Na+]>CN(C=O)C>[ClH:1].[ClH:1].[CH3:13][N:4]([CH3:3])[CH2:5][CH2:6][CH:7]1[CH2:12][CH2:11][N:10]([CH2:23][CH2:22][O:21][C:18]2[CH:19]=[CH:20][C:15]([CH3:14])=[CH:16][CH:17]=2)[CH2:9][CH2:8]1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 956671-(2-Bromoethoxy)-4-methylbenzeneHCID 19085438HCID 19085438, Verbindung

Produkt 1

HCID 190854514-(2-Dimethylaminoethyl)-1-[2-(4-methylphenoxy)ethyl]piperidine dihydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 4-(2-dimethylaminoethyl)piperidine dihydrochloride (7.0 g), 2-bromoethyl 4-methylphenyl ether (6.6 g), triethylamine (12.75 ml) and DMF (50 ml) was heated on a steam bath for 16 hours. The mixture was poured into ice/water (500 ml), basified with 2M sodium hydroxide solution and extracted with dichloromethane. The combined organic extracts were washed with water and then extracted with 2M hydrochloric acid. The combined acidic layers were basified with 2M sodium hydroxide solution and then extracted with dichloromethane to give an oil. The oil was distilled at 120° C. at 0.05 mbar and the distillate was dissolved in ether, acidified with ethereal hydrogen chloride solution and filtered. The solid obtained was washed with ether and recrystallised from absolute ethanol to give 4-(2-dimethylaminoethyl)-1-[2-(4-methylphenoxy)ethyl]piperidine dihydrochloride m.p. 281°-283° C.

Aufarbeitung

  1. temperaturewas heated on a steam bath for 16 hours
  2. extractionextracted with dichloromethane
  3. washThe combined organic extracts were washed with water
  4. extractionextracted with 2M hydrochloric acid
  5. extractionextracted with dichloromethane
  6. customto give an oil
  7. distillationThe oil was distilled at 120° C. at 0.05 mbar
  8. dissolutionthe distillate was dissolved in ether
  9. filtrationfiltered
  10. customThe solid obtained
  11. washwas washed with ether
  12. customrecrystallised from absolute ethanol

Quellen und Nachweise

ORD-Eintrag
ord-03b37c8bdad746dba7d4d4d045ee5353
Quelldatensatz
uspto-grants-1998_06
Patentnummer
US05760035

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