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3-Fluorobenzyl chloride → [4-(4-Fluorobenzyloxy)-1-phenylcyclohexyl]dimethylamine

HRID 1349396
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1349396
[CH3:1][N:2]([CH3:16])[C:3]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:8][CH2:7][CH:6]([OH:9])[CH2:5][CH2:4]1.[CH3:17][C:18]([CH3:21])([O-])[CH3:19].[K+].[F:23][C:24]1[CH:25]=C(C=C[CH:31]=1)CCl>CN(C)C=O>[F:23][C:24]1[CH:25]=[CH:21][C:18]([CH2:19][O:9][CH:6]2[CH2:7][CH2:8][C:3]([N:2]([CH3:16])[CH3:1])([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH2:4][CH2:5]2)=[CH:17][CH:31]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 99743-Fluorobenzyl chlorideHCID 111487094-Dimethylamino-4-phenylcyclohexanolHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 9949304[4-(4-Fluorobenzyloxy)-1-phenylcyclohexyl]dimethylamineAusbeute 34,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2.00 g of 4-dimethylamino-4-phenylcyclohexanol were dissolved in 20 ml of dimethylformamide; 1.13 g of potassium tert.-butoxide were added and stirring was carried out for 45 minutes, before 1.45 g of 3-fluorobenzyl chloride were added dropwise in the course of 15 minutes. After stirring overnight, the mixture was added to 25 ml of ice-water and extracted repeatedly with ethyl acetate. The combined extracts were washed with saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated. The resulting crude product (2.66 g) was separated on silica gel with hexane/diethyl ether (V:V=1:1). 1.02 g of [4-(4-fluorobenzyloxy)-1-phenylcyclohexyl]dimethylamine were obtained and, as described for Example 1, were converted into 1.05 g of the corresponding hydrochloride using chlorotrimethylsilane and water in 2-butanone.

Aufarbeitung

  1. additionwere added dropwise in the course of 15 minutes
  2. stirringAfter stirring overnight
  3. extractionextracted repeatedly with ethyl acetate
  4. washThe combined extracts were washed with saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting crude product (2.66 g) was separated on silica gel with hexane/diethyl ether (V:V=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-274edc1de25343a1844a0f7b2f1ce73c
Quelldatensatz
uspto-grants-2007_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07211694B2

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