Water → (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-yl-methyl)-4-(3-phenylpropyl)piperazine

HRID 1379193

Reaktionsgleichung

Reaktionsgleichung von HRID 1379193
[F:1][C:2]([F:32])([F:31])[C:3]1[CH:4]=[C:5]([CH:24]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:26]=1)[C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][C@H:9]1[CH2:14][C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[NH:17][CH:16]=1)=[O:7].Br[CH2:34][CH2:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O.ClCCl>[F:30][C:27]([F:28])([F:29])[C:25]1[CH:24]=[C:5]([CH:4]=[C:3]([C:2]([F:1])([F:31])[F:32])[CH:26]=1)[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:34][CH2:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH2:10][C@H:9]1[CH2:14][C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[NH:17][CH:16]=1)=[O:7]

Komponenten

7

Edukt 4

HCID 962WaterHCID 11430Potassium Carbonate2×HCID 12503(3-Bromopropyl)benzene2×HCID 10972505(2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-ylmethyl)piperazine

Produkt 1

HCID 86751295(2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-yl-methyl)-4-(3-phenylpropyl)piperazineAusbeute 79,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-yl-methyl)piperazine (0.17 g), 1-bromo-3-phenylpropane (0.08 g) and potassium carbonate (0.15 g) in dry dimethylformamide (10 ml) was stirred at room temperature under nitrogen atmosphere. After 2 hours, additional 1-bromo-3-phenylpropane (0.14 ml) and potassium carbonate (0.15 g) were added, and the mixture was stirred overnight. Water (50 ml) and dichloromethane (50 ml) were added to the mixture. The dichloromethane layer was washed with brine and dried over magnesium sulfate. After evaporation of the solvent, the residue was purified on a silica gel column (10 g) eluting with a mixture of toluene and ethyl acetate (4:1) to give (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-yl-methyl)-4-(3-phenylpropyl)piperazine (0.17 g) as a syrup.

Aufarbeitung

  1. stirringthe mixture was stirred overnight
  2. washThe dichloromethane layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customAfter evaporation of the solvent
  5. customthe residue was purified on a silica gel column (10 g)
  6. washeluting with a mixture of toluene and ethyl acetate (4:1)

Quellen und Nachweise

ORD-Eintrag
ord-c6fab44732b949439b676c24612572ed
Quelldatensatz
uspto-grants-1997_09
Patentnummer
US05670505

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