Potassium Phosphate, Tribasic → 1-[2-Methyl-5-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-phenyl]piperazine

HRID 2175073Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2175073
Cl[C:2]1[CH:3]=[CH:4][C:5]([CH3:14])=[C:6]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:7]=1.CC1(C)C(C)(C)OB([C:23]2[CH:32]=[CH:31][C:30]3[C:29]([CH3:34])([CH3:33])[CH2:28][CH2:27][C:26]([CH3:36])([CH3:35])[C:25]=3[CH:24]=2)O1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>C1COCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:14][C:5]1[CH:4]=[CH:3][C:2]([C:32]2[CH:23]=[CH:24][C:25]3[C:26]([CH3:36])([CH3:35])[CH2:27][CH2:28][C:29]([CH3:34])([CH3:33])[C:30]=3[CH:31]=2)=[CH:7][C:6]=1[N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1

Komponenten

7

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 693767N-(5-Chloro-2-methylphenyl)piperazineHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 112439294,4,5,5-Tetramethyl-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-1,3,2-dioxaborolane

Produkt 1

HCID 532523231-[2-Methyl-5-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-phenyl]piperazine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

100 mg (0.48 mmol) of 1-(5-chloro-2-methylphenyl)piperazine and 300 mg (0.95 mmol) and of 4,4,5,5-tetramethyl-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-1,3,2-dioxaborolane are dissolved in 2 ml of THF, 302 mg (1.43 mmol) of potassium phosphate, 3 mg of palladium acetate and 11 mg of 2-dicylcohexylphosphino-2′,4′,6′-tri-i-propyl-1,1′-biphenyl are added. The reaction mixture is degassed a number of times and stirred at 120° C. under nitrogen atmosphere for 4 h, subsequently diluted with water and extracted three times with ethyl acetate. The combined organic phases are dried over Na2SO4 and evaporated. The crude product is purified by means of preparative HPLC and converted into the hydrochloride using methanolic HCl.

Aufarbeitung

  1. customThe reaction mixture is degassed a number of times
  2. additionsubsequently diluted with water
  3. extractionextracted three times with ethyl acetate
  4. dry with materialThe combined organic phases are dried over Na2SO4
  5. customevaporated
  6. customThe crude product is purified by means of preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-b4e70e2f73b948d19dc9b5b5a2fb871e
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09062015B2

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