Triethylamine → HCID 178418330, Verbindung

HRID 1737933

Reaktionsgleichung

Reaktionsgleichung von HRID 1737933
[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.CN(C1C=CC=CN=1)C.[Cl:34][C:35]1[CH:43]=[CH:42][C:38]([C:39](Cl)=[O:40])=[CH:37][CH:36]=1.[OH-].[Na+]>C(Cl)Cl.O>[Cl:34][C:35]1[CH:43]=[CH:42][C:38]([C:39]([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:40])=[CH:37][CH:36]=1

Komponenten

8

Edukt 5

HCID 8471TriethylamineHCID 85014-Chlorobenzoyl chlorideHCID 14798Sodium HydroxideHCID 218852-DimethylaminopyridineHCID 178418380HCID 178418380, Verbindung

Produkt 1

HCID 178418330HCID 178418330, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

0.24 g (0.001 mol) of cis-4-(4-dimethylaminomethylphenyl)-cyclohexanol, 0.34 ml (0.0025 mol) of triethylamine and 0.12 g (0.001 mol) of dimethylaminopyridine are dissolved in 20 ml of methylene chloride, mixed with 0.175 g (0.001 mol) of 4-chlorobenzoylchloride and stirred for 12 hours at ambient temperature. The reaction mixture is combined with water and adjusted to pH 12-13 using sodium hydroxide solution. The methylene chloride phase is separated off, the aqueous phase is extracted several times with methylene chloride and the combined organic phases are washed with saturated saline solution, dried and evaporated down in vacuo. The residue is purified by column chromatography (aluminium oxide neutral, activity stage III, ICN; petroleum ether/ethyl acetate=45:1) White crystals. Melting point: 96-97° C. Yield: 0.27 g (73% of theory)

Aufarbeitung

  1. customThe methylene chloride phase is separated off
  2. extractionthe aqueous phase is extracted several times with methylene chloride
  3. washthe combined organic phases are washed with saturated saline solution
  4. customdried
  5. customevaporated down in vacuo
  6. customThe residue is purified by column chromatography (aluminium oxide neutral, activity stage III, ICN; petroleum ether/ethyl acetate=45:1) White crystals

Quellen und Nachweise

ORD-Eintrag
ord-e767f0709d4045e28d85c33d5f9210fc
Quelldatensatz
uspto-grants-1999_10
Patentnummer
US05962507

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