Tri-tert-butylphosphine tetrafluoroborate → 1-[4-Azetidin-1-yl-2-(4,4-dimethylcyclohexyl)phenyl]-4-butylpiperazine

HRID 32177

Reaktionsgleichung

Reaktionsgleichung von HRID 32177
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][CH3:17])[CH2:10][CH2:9]2)=[C:4]([CH:18]2[CH2:23][CH2:22][C:21]([CH3:25])([CH3:24])[CH2:20][CH2:19]2)[CH:3]=1.Cl.[NH:27]1[CH2:30][CH2:29][CH2:28]1.CC(C)([O-])C.[Na+].F[B-](F)(F)F.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C.O.C1(C)C(C)=CC=CC=1>[N:27]1([C:2]2[CH:7]=[CH:6][C:5]([N:8]3[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][CH3:17])[CH2:10][CH2:9]3)=[C:4]([CH:18]3[CH2:23][CH2:22][C:21]([CH3:25])([CH3:24])[CH2:20][CH2:19]3)[CH:3]=2)[CH2:30][CH2:29][CH2:28]1

Komponenten

9

Edukt 4

HCID 2734635Tri-tert-butylphosphine tetrafluoroborateHCID 12308726Azetidine hydrochlorideHCID 231417381-[4-Bromo-2-(4,4-dimethylcyclohexyl)phenyl]-4-butylpiperazineHCID 23676156Sodium t-butoxide

Produkt 1

HCID 597694311-[4-Azetidin-1-yl-2-(4,4-dimethylcyclohexyl)phenyl]-4-butylpiperazine

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 7237O-XyleneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 1-[4-bromo-2-(4,4-dimethylcyclohexyl)phenyl]-4-butylpiperazine (50 mg, 0.123 mmol) produced in Example (57b), azetidine hydrochloride (17 mg, 0.185 mmol), sodium t-butoxide (47 mg, 0.492 mmol), palladium(II) acetate (3 mg, 0.0123 mmol), tri-t-butylphosphonium tetrafluoroborate (11 mg, 0.0369 mmol) and xylene (1 mL) was stirred for 3 hours at an external temperature of 100° C. Water was added to the reaction mixture and extraction was performed with ethyl acetate. The separated organic layer was filtered through Celite. The solvent was distilled off by nitrogen stream to the filtrate. The resultant residue was purified by NH silica gel column chromatography (ethyl acetate/hexane) to give 1-[4-azetidin-1-yl-2-(4,4-dimethylcyclohexyl)phenyl]-4-butylpiperazine as a colorless solid.

Aufarbeitung

  1. filtrationThe separated organic layer was filtered through Celite
  2. distillationThe solvent was distilled off by nitrogen stream to the filtrate
  3. customThe resultant residue was purified by NH silica gel column chromatography (ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-33f191f7e03346e3b882e7d82f26d813
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425554B2

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