N,N-Dimethyl-3-((naphthalen-1-yl)oxy)-3-(thiophen-2-yl)propan-1-amine → (S)-(+)-N,N-Dimethyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine

HRID 1987511

Reaktionsgleichung

Reaktionsgleichung von HRID 1987511
[CH3:1][N:2]([CH3:22])[CH2:3][CH2:4][CH:5]([O:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1)[C:6]1[S:7][CH:8]=[CH:9][CH:10]=1.C1(C)C=CC(C([C@@](C(O)=O)(O)[C@@](C(C2C=CC(C)=CC=2)=O)(O)C(O)=O)=O)=CC=1>C(OCC)(=O)C>[CH3:22][N:2]([CH3:1])[CH2:3][CH2:4][C@H:5]([O:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1)[C:6]1[S:7][CH:8]=[CH:9][CH:10]=1

Komponenten

4

Edukt 2

HCID 11573192N,N-Dimethyl-3-((naphthalen-1-yl)oxy)-3-(thiophen-2-yl)propan-1-amineHCID 29414711Di-para-toluoyl-L-tartaric acid

Produkt 1

HCID 9818212(S)-(+)-N,N-Dimethyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To 120 ml ethyl acetate is added 10 g (0.032 moles) of racemic N,N-Dimethyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine, followed by 5.95 g (0.015 moles) of Di-para-toluoyl-L-tartaric acid at 25° C.-28° C. The resultant clear solution is stirred at room temperature for about 2-3 hrs so as to crystallise the acid addition salt of the desired enantiomer of N,N-dimethyl-3-(1-naphthalenyloxy)-3-(2-thienyl)-propanamine. The product is filtered, washed with 100 ml ethyl acetate and dried at 60-70° C. Yield: 7.8 g, about 98% ee.

Aufarbeitung

  1. customto crystallise
  2. additionthe acid addition salt of the desired enantiomer of N,N-dimethyl-3-(1-naphthalenyloxy)-3-(2-thienyl)-propanamine
  3. filtrationThe product is filtered
  4. washwashed with 100 ml ethyl acetate
  5. customdried at 60-70° C

Quellen und Nachweise

ORD-Eintrag
ord-f5573cdb20b94d43aeb317318e6fdb1d
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07550605B2

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