3,4-Dimethoxyphenyl methyl ketone → 1-[4-Chloro-3-(trifluoromethyl)phenyl]-4-[1-(3,4-dimethoxyphenyl)ethyl]piperazine

HRID 1294607Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1294607
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][C:3]=1[C:14]([F:17])([F:16])[F:15].[CH3:18][C:19]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH3:30])[CH:22]=1)=O>CC(O[Ti](OC(C)C)(OC(C)C)OC(C)C)C.CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH:19]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH3:30])[CH:22]=3)[CH3:18])[CH2:10][CH2:9]2)=[CH:4][C:3]=1[C:14]([F:15])([F:17])[F:16]

Komponenten

5

Edukt 2

HCID 143283,4-Dimethoxyphenyl methyl ketoneHCID 27781371-(4-Chloro-3-(trifluoromethyl)phenyl)piperazine

Produkt 1

HCID 101374521-[4-Chloro-3-(trifluoromethyl)phenyl]-4-[1-(3,4-dimethoxyphenyl)ethyl]piperazine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178460666HCID 178460666, VerbindungKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A quantity of 0.17 g (0.6 mmole, 1 eq) of 1-(4-chloro-3-trifluoromethyl-phenyl)-piperazine and 0.1 g (0.6 mmole, 1 eq) of 3,4-dimethoxyacetophenone and 2 mL of Ti(OiPr)4 are warmed to 70° C. for 2 hours. The reaction solution is cooled to room temperature and 20 mL of anhydrous methanol is added followed by 1.0 g of NaBH and the resulting solution is stirred at room temperature for 2 hours. The reaction is quenched by the addition of 1 N NaOH and extracted with CH2Cl2. The CH2Cl2 extracts are dried over anhydrous MgSO4 and concentrated in vacuo. The residue is chromatographed on SiO2 with ethyl to afford 1-[4-chloro-3-(trifluoromethyl)phenyl]-4-[1-(3,4-dimethoxyphenyl)ethyl]piperazine (compound 2). Analysis 1H NMR (400 MHz, CDCl3): 7.31 (1H, d), 7.19 (1H, m), 6.90 (4H, m), 3.89 (6H, d), 3.38 (1H, m), 3.20 (4H, m), 2.61 (4H, m). MS (LC-MS): Calculated for C21H24ClF3N2O2 428.88. Found 429.30 (M+).

Aufarbeitung

  1. customThe reaction is quenched by the addition of 1 N NaOH
  2. extractionextracted with CH2Cl2
  3. dry with materialThe CH2Cl2 extracts are dried over anhydrous MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue is chromatographed on SiO2 with ethyl

Quellen und Nachweise

ORD-Eintrag
ord-c1ab1733162b4b65943b173d641382e0
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07241765B2

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