Methanol → Sodium [4-(3,3-diphenylpropyl)homopiperazine-1-yl]acetate

HRID 2119362Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2119362
[C:1]1([CH:7]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:8][CH2:9][N:10]2[CH2:16][CH2:15][CH2:14][N:13]([CH2:17][C:18]([O:20]C)=[O:19])[CH2:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO.[OH-].[Na+:31]>O1CCOCC1>[C:22]1([CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:8][CH2:9][N:10]2[CH2:16][CH2:15][CH2:14][N:13]([CH2:17][C:18]([O-:20])=[O:19])[CH2:12][CH2:11]2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1.[Na+:31]

Komponenten

5

Edukt 3

HCID 887MethanolHCID 14798Sodium Hydroxide2×HCID 54512635Methyl [4-(3,3-diphenylpropyl)homopiperazine-1-yl]acetate

Produkt 1

HCID 23718564Sodium [4-(3,3-diphenylpropyl)homopiperazine-1-yl]acetateAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Methyl [4-(3,3-diphenylpropyl)homopiperazine-1-yl]acetate (0.327 g, 0.89 mmol) was dissolved in a mixture of dioxane (3.1 mL). MeOH (1.1 mL) and 4N NaOH (0.22 mL). After stirring for 30 min. 5 more drops of 4N NaOH were added and stirring was, continued until hydrolysis of the methyl ester was complete. The mixture was concentrated in vacuo and the residue subjected to flash silica gel column chromatography (eluent: CH2Cl2/MeOH, 1/1, v/v) to give sodium [4-(3,3-diphenylpropyl)homopiperazine-1-yl]acetate (0.278 g) in 88% yield, TLC Rf=0.22 (10% CH3OH—CH2Cl2); RPLC tR=1.98 min (>85%), 220 nm (Method B); ESI/MS m/e 353.3 (M++H, C22H29N2O2).

Aufarbeitung

  1. stirringstirring
  2. concentrationThe mixture was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1ea48a530a694e87b7bf4e27565d6156
Quelldatensatz
uspto-grants-2004_02
Patentnummer
US06686353B1

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