Hydrochloric Acid → HCID 18924114, Verbindung

HRID 1290547Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1290547
[CH3:1][N:2]([CH3:28])[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:27]=[CH:26][C:16]([O:17][CH2:18][CH2:19][CH2:20][C:21]([O:23]CC)=[O:22])=[CH:15][CH:14]=1.[OH-].[Na+].Cl>CO>[CH3:28][N:2]([CH3:1])[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([O:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])=[CH:26][CH:27]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18918492HCID 18918492, Verbindung

Produkt 1

HCID 18924114HCID 18924114, VerbindungAusbeute 60,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of ethyl 4-[4-[3-(4-dimethylaminopyrid-3-yl)propyloxy]phenoxy]butyrate (160 mg) in methanol (10 ml) was added sodium hydroxide solution (2.0 ml of 1.0M) and the solution left until all starting ester had disappeared (Tlc). The reaction mixture was neutralised with hydrochloric acid (2.0 ml) of 1.0M) and evaporated in vacuo. A small amount (5 ml) of water was added and the resulting solution extracted with dichloromethane (3×15 ml). The organic extracts were combined, dried (PS paper) and evaporated to yield the title compound as colourless prisms, (90 mg) m.p. 106°-108° C. (from ethyl acetate); NMR (d6DMSO) δ 1.8-2.1(2H,q;2H,q); 2.4(2H,t); 2.8(2H,t;6H,s); 3.9(2H,t;2H,t); 6.8(5H,m); 8.2(2H,d); m/e 359 (M+H)+ ; calculated for C20 H26N2O4 : C,67.0;H,7.3;N, 7.8; found: C,67.1;H,7.6;N, 7.7%.

Aufarbeitung

  1. customevaporated in vacuo
  2. additionA small amount (5 ml) of water was added
  3. extractionthe resulting solution extracted with dichloromethane (3×15 ml)
  4. customdried (PS paper)
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-143e335f108f4811b5c1a2ab99e9bb91
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05750754

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