Piperazine, hexahydrate → 1-[3-(2-Phenoxyethoxy)-2-pyridinyl]piperazine, Dihydrochloride

HRID 493338Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 493338
[Cl:1][C:2]1[C:7]([O:8][CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.O.O.O.O.O.O.[NH:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1>O>[ClH:1].[ClH:1].[O:11]([CH2:10][CH2:9][O:8][C:7]1[C:2]([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)=[N:3][CH:4]=[CH:5][CH:6]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

4

Edukt 2

HCID 120181Piperazine, hexahydrateHCID 235095692-Chloro-3-(2-phenoxyethoxy)pyridine

Produkt 1

HCID 1317235561-[3-(2-Phenoxyethoxy)-2-pyridinyl]piperazine, Dihydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
165 °C

Versuchsvorschrift

A mixture of the product from Step 1 above (0.84 g, 3.1 mmol) and piperazine hexahydrate (5.3 g, 27.3 mmol) was heated in a sealed tube at 165° C. for 1 h. After cooling, the mixture was diluted with water (100 mL) and extracted twice with EtOAc. The combined and dried (MgSO4) organic phases were concentrated in vacuo and the residue was purified by chromatography on silica gel using CHCl3/MeOH/NH4OH (90.10-0 4) as eluent to give the free base of the title compound. The free base was treated with HCl/ether, and the resulting dihydrochloride salt was dried (80° C., 1 mmHg) to afford 0 598 g (52%) of the title compound as a light yellow solid mp 91-120° C. Anal. (C17H21N3O2.2HCl) C, H, N

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionextracted twice with EtOAc
  3. dry with materialdried (MgSO4) organic phases
  4. concentrationwere concentrated in vacuo
  5. customthe residue was purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-a7e607b9f6cc4b518a2e63fa02794200
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07534794B2

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