18-Crown-6 → N,N-Dimethyl-3-((naphthalen-1-yl)oxy)-3-(thiophen-2-yl)propan-1-amine

HRID 2234230

Reaktionsgleichung

Reaktionsgleichung von HRID 2234230
C(O[K])(C)(C)C.C1OCCOCCOCCOCCOCCOC1.[CH3:25][N:26]([CH2:28][CH2:29][C@H:30]([O:36][C:37]1[C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[CH:40]=[CH:39][CH:38]=1)[C:31]1[S:32][CH:33]=[CH:34][CH:35]=1)[CH3:27]>S1(CCCC1)(=O)=O>[CH3:25][N:26]([CH2:28][CH2:29][CH:30]([O:36][C:37]1[C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[CH:40]=[CH:39][CH:38]=1)[C:31]1[S:32][CH:33]=[CH:34][CH:35]=1)[CH3:27]

Komponenten

5

Edukt 3

HCID 2855718-Crown-6HCID 9818212(S)-(+)-N,N-Dimethyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamineHCID 178418922HCID 178418922, Verbindung

Produkt 1

HCID 11573192N,N-Dimethyl-3-((naphthalen-1-yl)oxy)-3-(thiophen-2-yl)propan-1-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31347SulfolaneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

tBuOK (16.8 g), and 18-crown-6 (0.25 g) are added to a solution of (S)-N,N-dimethyl-3-(naphthyloxy)-3-(2-thienyl)propylamine (31 g) in sulfolane (100 ml), bubbled with a moderate stream of nitrogen, and the mixture is stirred and heated at 110° C. for 2 hours. After cooling down to lab temperature, the mixture is diluted with water (300 ml) and the racemic product is extracted with toluene. After evaporation, 25 g (81%) of RS)-N-methyl-3-(naphthyloxy)-3-(2-thienyl)propylamine is obtained.

Aufarbeitung

  1. custombubbled with a moderate stream of nitrogen
  2. temperatureAfter cooling down to lab temperature
  3. additionthe mixture is diluted with water (300 ml)
  4. extractionthe racemic product is extracted with toluene
  5. customAfter evaporation, 25 g (81%) of RS)-N-methyl-3-(naphthyloxy)-3-(2-thienyl)propylamine
  6. customis obtained

Quellen und Nachweise

ORD-Eintrag
ord-779cc6060383413d999ea845235342a3
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07709662B2

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