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Dimethyl Sulfoxide → (S)-2-methyl-3-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-propionaldehyde

HRID 511115
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 511115
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][C@@H:12]([CH2:15][N:16]1[CH2:21][CH2:20][N:19]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=2)[CH2:18][CH2:17]1)[CH2:13][OH:14].C(N(CC)CC)C>ClCCl.O>[CH3:11][C@@H:12]([CH2:15][N:16]1[CH2:21][CH2:20][N:19]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:30])([F:29])[F:31])=[CH:24][CH:23]=2)[CH2:18][CH2:17]1)[CH:13]=[O:14]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 58576864(S)-2-methyl-3-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-propan-1-ol

Produkt 1

HCID 58576376(S)-2-methyl-3-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-propionaldehydeAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel3×

Reaktionsbedingungen

Temperatur
-70 °C

Versuchsvorschrift

A 2 M solution of oxalyl dichloride in dichloromethane (4.96 mL; 13.2 mmol) is diluted with dichloromethane (35 mL); is cooled to −70° C. and dimethylsulfoxide (0.94 mL; 13.2 mmol) is added. The resulting mixture is stirred for 20 minutes. The temperature is allowed to reach −60° C. and a solution of (S)-2-methyl-3-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-propan-1-ol (2.0 g; 6.6 mmol, prepared in accordance with Example 65) in dichloromethane (20 mL) is added over 5 minutes. The resulting mixture is stirred at −60° C. for 2 hours before triethylamine (4.61 mL; 33.1 mmol) is added. After 10 minutes reaction time, the reaction mixture is allowed to slowly reach room temperature. The reaction is treated with water (100 mL), the organic layer is separated and is washed with water (2×100 mL) and concentrated to afford the desired product (1.99 g; 6.6 mmol). The crude product is engaged in the next step without further purification.

Aufarbeitung

  1. customto reach −60° C.
  2. additionis added
  3. customAfter 10 minutes reaction time
  4. customis allowed to slowly reach room temperature
  5. customthe organic layer is separated
  6. washis washed with water (2×100 mL)
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-d826a61fb7b54dd6a4bcc392b14fe800
Quelldatensatz
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09096524B2

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