Bicyclo(2.2.1)hept-5-ene-2-carboxaldehyde → 1-Bicyclo[2.2.1]hept-5-en-2-ylmethyl-4-(5-chloro-2-methoxy-phenyl)-2-methyl-piperazine

HRID 229355

Reaktionsgleichung

Reaktionsgleichung von HRID 229355
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:15][CH3:16])=[C:6]([N:8]2[CH2:13][CH2:12][NH:11][CH:10]([CH3:14])[CH2:9]2)[CH:7]=1.[CH:17]12[CH2:23][CH:20]([CH:21]=[CH:22]1)[CH2:19][CH:18]2[CH:24]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH:17]12[CH2:23][CH:20]([CH:21]=[CH:22]1)[CH2:19][CH:18]2[CH2:24][N:11]1[CH2:12][CH2:13][N:8]([C:6]2[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[O:15][CH3:16])[CH2:9][CH:10]1[CH3:14]

Komponenten

5

Edukt 3

HCID 95117Bicyclo(2.2.1)hept-5-ene-2-carboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 577583751-(5-Chloro-2-methoxy-phenyl)-3-methyl-piperazine

Produkt 1

HCID 577583811-Bicyclo[2.2.1]hept-5-en-2-ylmethyl-4-(5-chloro-2-methoxy-phenyl)-2-methyl-piperazine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

48 mg (0.2 mmol) of 1-(5-Chloro-2-methoxy-phenyl)-3-methyl-piperazine was dissolved in 1.5 mL anhydrous 1,2-dichloroethane. 5-Norbornene-2-carboxaldehyde (25 mg, 0.2 mmol) was added, followed by followed by 63 mg (0.3 mmol) sodium triacetoxyborohydride [NaBH(OAc)3]. The reaction was stirred overnight, then quenched with 1.0 mL DMSO:methanol (1:1). The reaction mixture was filtered and purified by reverse-phase HPLC (2-99CH3CN in 0.085% TFA (aq), 50 mL/min, 2.0 mL injected), and the product 1-bicyclo[2.2.1]hept-5-en-2-ylmethyl-4-(5-chloro-2-methoxy-phenyl)-2-methyl-piperazine isolated as the mono-TFA salt. Theoretical (M+H)+ m/z=347.9; Found 348.0.

Aufarbeitung

  1. customquenched with 1.0 mL DMSO:methanol (1:1)
  2. filtrationThe reaction mixture was filtered
  3. custompurified by reverse-phase HPLC (2-99CH3CN in 0.085% TFA (aq), 50 mL/min, 2.0 mL injected)

Quellen und Nachweise

ORD-Eintrag
ord-99ff7fb4f92f4ab39a94c9207ba5862e
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07563795B2

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