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Acetic Acid → HCID 9830391, Verbindung

HRID 2229804
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2229804
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([CH:6]([N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[C:21](O)(=O)[CH3:22].[CH:25](=O)[CH2:26][CH:27]=O.[C:30]([BH3-])#[N:31].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]([N:13]2[CH2:14][CH2:15][N:16]([CH2:25][CH2:26][CH2:27][N:13]3[CH2:6][CH2:7][N:31]([CH:30]([C:21]4[CH:22]=[CH:8][CH:9]=[CH:10][CH:11]=4)[C:5]4[CH:4]=[CH:3][C:2]([Cl:1])=[CH:20][CH:19]=4)[CH2:15][CH2:14]3)[CH2:17][CH2:18]2)[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[CH:19][CH:20]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 9340NorchlorcyclizineHCID 10964MalonaldehydeHCID 5003444Sodium cyanoborohydride

Produkt 1

HCID 9830391HCID 9830391, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 1-(4-chlorobenzhydryl)piperazine 1 (obt. from Aldrich; 2 mmols) in methanol (8 mL) is acidified with acetic acid to pH 6.5 (pH meter) under a nitrogen atmosphere. Malonaldehyde (1 mmol) is added neat followed by sodium cyanoborohydride (3.1 mmols). The progress of the reaction is followed by thin layer chromatography. After the reaction is complete, the reaction solution is quenched in water and the pH of the aqueous mixture is adjusted to greater than 10 with aqueous NaOH. The mixture is extracted with ether, the organic extracts are washed with half-saturated saline, dried (Na2SO4), filtered and concentrated under reduced pressure to give the crude product. The desired compound 1,3-bis-[4-(4-chlorobenzhydryl)piperazin-1-yl]propane 2 (R=—CH2—; R1=Cl; R2=H) is obtained by purification of the crude product with the use of HPLC.

Aufarbeitung

  1. customthe reaction solution is quenched in water
  2. extractionThe mixture is extracted with ether
  3. washthe organic extracts are washed with half-saturated saline
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto give the crude product

Quellen und Nachweise

ORD-Eintrag
ord-def05c55434d458789a221048290577f
Quelldatensatz
uspto-grants-2002_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06420560B1

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