1-(2-Methoxyphenyl)piperazine → 3-[4-(2-Methoxy-phenyl)-piperazin-1-ylmethyl]-piperidine-1-carboxylic acid tert-butyl ester

HRID 50655

Reaktionsgleichung

Reaktionsgleichung von HRID 50655
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14]OS(C)(=O)=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH3:26][O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[N:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1>C(#N)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][N:37]2[CH2:36][CH2:35][N:34]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=3[O:27][CH3:26])[CH2:39][CH2:38]2)[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Komponenten

5

Edukt 3

HCID 13461-(2-Methoxyphenyl)piperazineHCID 11430Potassium CarbonateHCID 22647269tert-Butyl 3-(((methylsulfonyl)oxy)methyl)piperidine-1-carboxylate

Produkt 1

HCID 213032013-[4-(2-Methoxy-phenyl)-piperazin-1-ylmethyl]-piperidine-1-carboxylic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of 3-methanesulfonyloxymethyl-piperidine-1-carboxylic acid tert-butyl ester (11.06 g, 0.04 mol) in acetonitrile (180 mL) was added potassium carbonate (26 g, 0.19 mol) followed by 1-(2-methoxy-phenyl) piperazine (7.25 g, 0.04 mol). After completion of addition the reaction mixture was heated to reflux. After 12 h the reaction mixture was cooled down to room temperature and quenched with water. The aqueous layer was extracted with ethyl acetate (3×100 mL). The combined organic layers were dried over sodium sulfate and concentrated to yield an oil. This crude material was purified using silica gel chromatography (7:3:0.05 Hexane:EtOAc:2M NH3 in EtOH) to afford the desired compound in good yield (8.0 g, 55%). C22H35N3O3,LRMS (m/z)=390 (MH+).

Aufarbeitung

  1. additionAfter completion of addition the reaction mixture
  2. temperaturewas heated to reflux
  3. customquenched with water
  4. extractionThe aqueous layer was extracted with ethyl acetate (3×100 mL)
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. concentrationconcentrated
  7. customto yield an oil
  8. customThis crude material was purified

Quellen und Nachweise

ORD-Eintrag
ord-8ae9b22ad09f41dfbaab188226486b1d
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713479B2

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