Hydrochloric Acid → HCID 18955939, Verbindung

HRID 2379680Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2379680
Br[C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][CH:22]=1)[CH:5]([N:13]1[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]1)[C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1.C([Li])CCC.CN(C)[CH:30]=[O:31].Cl>O1CCCC1.CCCCCC>[Cl:12][C:9]1[CH:10]=[CH:11][C:6]([CH:5]([N:13]2[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]2)[C:4]2[CH:20]=[CH:21][CH:22]=[C:2]([CH:30]=[O:31])[CH:3]=2)=[CH:7][CH:8]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 189559271-[(3-Bromophenyl)(4-chlorophenyl)methyl]-4-methylpiperazineHCID 178418339Butyllithium

Produkt 1

HCID 18955939HCID 18955939, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

1-(3-Bromo-4'-chlorobenzhydryl)-4-methylpiperazine (see U.S. Pat. No. 4,757,074) (1.00 g, 2.63 mmole) was dissolved in 12 ml of dry tetrahydrofuran under nitrogen and cooled to -78° C. A solution of 1.1 M n-butyllithium in hexane (2.4 ml) was added dropwise and the reaction was stirred for ten minutes. N,N-Dimethylformamide (0.25 ml, 3.2 mmole) was added in one portion and the reaction was allowed to warm to -40° C. Hydrochloric acid (1.0M, 20 ml) was added and the reaction was warmed to room temperature. The solution was washed with 20 ml of diethyl ether and the ethereal wash was discarded. The aqueous solution was made basic with aqueous sodium hydroxide and extracted with two 15 ml portions of chloroform. The combined chloroform extracts were dried over sodium sulfate and the solvent removed to give 738 mg of crude 1-(4-chloro-3'-formylbenzhydryl)-4-methylpiperazine as a dark oil.

Aufarbeitung

  1. temperatureto warm to -40° C
  2. temperaturethe reaction was warmed to room temperature
  3. washThe solution was washed with 20 ml of diethyl ether
  4. washthe ethereal wash
  5. extractionextracted with two 15 ml portions of chloroform
  6. dry with materialThe combined chloroform extracts were dried over sodium sulfate
  7. customthe solvent removed

Quellen und Nachweise

ORD-Eintrag
ord-bd3d815c664e46c68c79748597a7ac43
Quelldatensatz
uspto-grants-1994_11
Patentnummer
US05364843

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