Benzoyl chloride → N-(4-benzyl-4-dimethylaminocyclohexyl)-N-propylbenzamide hydrochloride

HRID 1179035Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1179035
[CH2:1]([C:8]1([N:18]([CH3:20])[CH3:19])[CH2:13][CH2:12][CH:11]([NH:14][CH2:15][CH2:16][CH3:17])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:28]([Cl:36])(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[OH-].[K+]>C(Cl)Cl.CN(C)C1C=CN=CC=1.O>[ClH:36].[CH2:1]([C:8]1([N:18]([CH3:20])[CH3:19])[CH2:13][CH2:12][CH:11]([N:14]([CH2:15][CH2:16][CH3:17])[C:28](=[O:35])[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

8

Edukt 4

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 14797Potassium HydroxideHCID 210989801-benzyl-N,N-dimethyl-N'-propylcyclohexane-1,4-diamine

Produkt 1

HCID 69338285N-(4-benzyl-4-dimethylaminocyclohexyl)-N-propylbenzamide hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

700 mg of the nonpolar diastereomer of 1-benzyl-N,N-dimethyl-N′-propyl-cyclohexane-1,4-diamine were dissolved in 10 ml methylene chloride, and 370 μl triethylamine and approx. 10 mg DMAP (4-dimethylaminopyridine) were added. 311 μl benzoyl chloride were added dropwise, while cooling in an ice/methanol bath, and the reaction mixture was then stirred overnight, while warming to room temperature. For working up, 10 ml five molar KOH solution and 10 ml water were added, the mixture was stirred for ten minutes and extracted three times with 20 ml methylene chloride each time, the combined extracts were dried over magnesium sulfate and filtered and the filtrate was concentrated. From the crude product obtained (834 mg), 909 mg N-(4-benzyl-4-dimethylamino-cyclohexyl)-N-propyl-benzamide hydrochloride were prepared as described for example 1 with water and chlorotrimethylsilane in 2-butanone.

Aufarbeitung

  1. temperaturewhile cooling in an ice/methanol bath
  2. stirringthe mixture was stirred for ten minutes
  3. extractionextracted three times with 20 ml methylene chloride each time
  4. dry with materialthe combined extracts were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-a2e120059db54a5a8a7c170f8420c055
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07276518B2

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