Sodium Carbonate → 1-(3,4,5-Trimethoxybenzoyl)-3-(3,4-dichlorophenyl)-3-(2-hydroxyethyl)piperidine

HRID 323254Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 323254
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:15][CH2:16][OH:17])[CH2:14][CH2:13][CH2:12][NH:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].C(=O)([O-])[O-].[Na+].[Na+].[CH3:24][O:25][C:26]1[CH:27]=[C:28]([CH:32]=[C:33]([O:37][CH3:38])[C:34]=1[O:35][CH3:36])[C:29](Cl)=[O:30]>C(OCC)(=O)C.O>[CH3:38][O:37][C:33]1[CH:32]=[C:28]([CH:27]=[C:26]([O:25][CH3:24])[C:34]=1[O:35][CH3:36])[C:29]([N:11]1[CH2:12][CH2:13][CH2:14][C:9]([C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)([CH2:15][CH2:16][OH:17])[CH2:10]1)=[O:30]

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 154604002-[3-(3,4-Dichlorophenyl)piperidin-3-yl]ethanol

Produkt 1

HCID 184645141-(3,4,5-Trimethoxybenzoyl)-3-(3,4-dichlorophenyl)-3-(2-hydroxyethyl)piperidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 22728543Water ethylacetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Combine 3-(3,4-dichlorophenyl)-3-(2-hydroxyethyl)piperidine (1.08 g, 3.94 mmol) and sodium carbonate (0.21 g, 2.00 mmol) in 1/1 ethyl acetate/water (50 mL). Cool the reaction mixture to 0° C. with an ice bath. Add 3,4,5-trimethoxybenzoyl chloride (0.83 g, 3.58 mmol). Warm to ambient temperature. After 18 hours, separate the layers and extract the aqueous layer three times with ethyl acetate. Dry the combined organic layers over Na2SO4, filter, and concentrate in vacuo to obtain a residue. Chromatograph the residue on silica gel to give the title compound: Rf=0.5 (silica gel, 1/1 ethyl acetate/hexane). Elemental Analysis calculated for C23H27Cl2NO5: C 58.97; H 5.81; N 2.99; Found C 58.85; H 5.90; N 2.96.

Aufarbeitung

  1. temperatureWarm to ambient temperature
  2. customseparate the layers
  3. extractionextract the aqueous layer three times with ethyl acetate
  4. dry with materialDry the combined organic layers over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo
  7. customto obtain a residue

Quellen und Nachweise

ORD-Eintrag
ord-6ceae20135db4b2dbae96572f29feaca
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06211199B1

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