1-Phenylpiperazine → 1-(3-(1-tert-butyl-5-phenyl-1H-pyrazol-3-yl)propyl)-4-phenylpiperazine

HRID 883277Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 883277
[C:1]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:8][C:7]([CH2:16][CH2:17][CH:18]=O)=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[C:20]1([N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(N(C(C)C)CC)(C)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl.CCCCCC.CCOC(C)=O.O>[C:1]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:8][C:7]([CH2:16][CH2:17][CH2:18][N:29]2[CH2:30][CH2:31][N:26]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:27][CH2:28]2)=[N:6]1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

9

Edukt 4

HCID 70961-PhenylpiperazineHCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 866399163-(1-tert-butyl-5-phenyl-1H-pyrazol-3-yl)propanal

Produkt 1

HCID 250646411-(3-(1-tert-butyl-5-phenyl-1H-pyrazol-3-yl)propyl)-4-phenylpiperazine

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8058HexaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

3-(1-tert-butyl-5-phenyl-1H-pyrazol-3-yl)propanal (80 mg, 312 mmol) and 1-phenylpiperazine (0.047 mL, 0.312 mmol) were dissolved in 5 mL of CH2Cl2, and then 0.7 g of 4 Å molecular sieve powder was added thereto and stirred. Diisopropylethylamine (DIPEA; 54 mL, 0.312 mmol) was slowly added thereto, and stirred for 30 min at room temperature. Then, NaBH(OAc)3 (231 mg, 1.092 mmol) was added thereto and stirred for 12 hours at room temperature. The reaction progress and completion were confirmed by TLC. Upon completion of the reaction, water (0.1 mL) was added to the reaction mixture and then stirred for 3 min. 81 mg (64%) of target compound was obtained via column chromatography (EtOAc:Hexane=4:1, v/v).

Aufarbeitung

  1. addition0.7 g of 4 Å molecular sieve powder was added
  2. stirringstirred for 30 min at room temperature
  3. stirringstirred for 12 hours at room temperature
  4. additionwas added to the reaction mixture
  5. stirringstirred for 3 min

Quellen und Nachweise

ORD-Eintrag
ord-b1b476a0cace40ab9c3df65deceb3e88
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08236806B2

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