Triethylamine → 5-Oxo-5-(4-phenylpiperazin-1-yl)pentanal

HRID 1942406Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1942406
C(Cl)(=O)C(Cl)=O.[OH:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([N:14]1[CH2:19][CH2:18][N:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:16][CH2:15]1)=[O:13].C(N(CC)CC)C>ClCCl.CS(C)=O.[Cl-].[Na+].O>[O:13]=[C:12]([N:14]1[CH2:15][CH2:16][N:17]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:18][CH2:19]1)[CH2:11][CH2:10][CH2:9][CH:8]=[O:7]

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 669376015-Hydroxy-1-(4-phenylpiperazin-1-yl)pentan-1-one

Produkt 1

HCID 866513155-Oxo-5-(4-phenylpiperazin-1-yl)pentanal

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 679Dimethyl SulfoxideLösungsmittel2×HCID 6344DichloromethaneLösungsmittel3×HCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

A solution of 1.11 mL (12.8 mmol) oxalyl chloride in 35 mL of dichloromethane is cooled to −80° C. under argon atmosphere. 2.33 mL (32.7 mmol) of dimethylsulfoxide in 9.33 mL of dichloromethane is introduced dropwise over 10 minutes. After 5 minutes a solution of 1.84 (7 mmol) 5-hydroxy-1-(4-phenylpiperazin-1-yl)pentan-1-one in 8 mL dichloromethane and 2 mL dimethylsulfoxide is added over the course of 10 minutes. The reaction mixture is stirred for another hour at −80° C. before 5 mL of triethylamine is added and the mixture is allowed to warm up to room temperature. 50 mL of saturated brine solution is added for hydrolysis. The organic phase is separated, extracted three times with a saturated solution of sodium chloride, dried over sodium sulfate and the solvent is evaporated. The crude product is obtained in almost quantitative yield.

Aufarbeitung

  1. additionis added
  2. customThe organic phase is separated
  3. extractionextracted three times with a saturated solution of sodium chloride
  4. dry with materialdried over sodium sulfate
  5. customthe solvent is evaporated

Quellen und Nachweise

ORD-Eintrag
ord-d48f935d23634ba298dd4290c79c7b38
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08389555B2

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