Triethylamine → HCID 178418352, Verbindung

HRID 1651

Reaktionsgleichung

Reaktionsgleichung von HRID 1651
[CH3:1][N:2]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C@H:11]2[CH2:16][CH2:15][C@H:14]([OH:17])[CH2:13][CH2:12]2)=[CH:7][CH:6]=1)[CH3:3].C(N(CC)CC)C.[Cl:25][C:26]1[CH:34]=[CH:33][C:29]([C:30](Cl)=[O:31])=[CH:28][CH:27]=1.[OH-].[Na+]>C(Cl)Cl.O>[Cl:25][C:26]1[CH:34]=[CH:33][C:29]([C:30]([O:17][C@H:14]2[CH2:15][CH2:16][C@H:11]([C:8]3[CH:9]=[CH:10][C:5]([CH2:4][N:2]([CH3:1])[CH3:3])=[CH:6][CH:7]=3)[CH2:12][CH2:13]2)=[O:31])=[CH:28][CH:27]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 85014-Chlorobenzoyl chlorideHCID 14798Sodium HydroxideHCID 178418401HCID 178418401, Verbindung

Produkt 1

HCID 178418352HCID 178418352, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 1.0 g (0.0043 mol) of trans-4-(4-dimethylaminomethylphenyl)-cyclohexanol and 0.6 ml of triethylamine in 50 ml of methylene chloride is combined, dropwise, with 0.75 g (0.0043 mol) of 4-chlorobenzoylchloride, with stirring, and refluxed for 3 hours. After cooling, 50 ml of water are added, the mixture is adjusted to pH 12-13 with sodium hydroxide solution, the methylene chloride phase is separated off and the aqueous phase is extracted once more with methylene chloride. The combined organic phases are dried over sodium sulphate and evaporated down in vacuo. The solid residue is purified by column chromatography (aluminium oxide neutral, activity stage III, ICN; petroleum ether/ethyl acetate=40:1). White crystals are obtained with a melting point of 94°-95° C.

Aufarbeitung

  1. temperaturerefluxed for 3 hours
  2. temperatureAfter cooling
  3. customthe methylene chloride phase is separated off
  4. extractionthe aqueous phase is extracted once more with methylene chloride
  5. dry with materialThe combined organic phases are dried over sodium sulphate
  6. customevaporated down in vacuo
  7. customThe solid residue is purified by column chromatography (aluminium oxide neutral, activity stage III, ICN; petroleum ether/ethyl acetate=40:1)
  8. customWhite crystals are obtained with a melting point of 94°-95° C.

Quellen und Nachweise

ORD-Eintrag
ord-fe8da988a6f64ed0968009c91353edde
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05726205

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