Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate → 2-[1-(4-Acetyl-phenyl)-piperidin-4-yl]-1-(4-cyclobutyl-piperazin-1-yl)-ethanone

HRID 2262707Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2262707
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][CH:13]([CH2:16][C:17]([OH:19])=O)[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH:20]1([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[CH2:24][CH2:23][CH2:22]C1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>C(Cl)Cl>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:11][CH2:12][CH:13]([CH2:16][C:17]([N:28]3[CH2:27][CH2:26][N:25]([CH:20]4[CH2:22][CH2:23][CH2:24]4)[CH2:30][CH2:29]3)=[O:19])[CH2:14][CH2:15]2)=[CH:8][CH:9]=1)(=[O:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 8064211-CyclopentylpiperazineHCID 49759600[1-(4-Acetyl-phenyl)-piperidin-4-YL]-acetic acid

Produkt 1

HCID 574424042-[1-(4-Acetyl-phenyl)-piperidin-4-yl]-1-(4-cyclobutyl-piperazin-1-yl)-ethanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of [1-(4-acetyl-phenyl)-piperidin-4-yl]-acetic acid (0.11 mmol) in anhydrous DCM (2 mL) is added 1-cyclopentylpiperazine (1.1 eq.), TEA (0.22 mmol), and BOP (0.14 mmol). The resulting mixture is stirred at rt overnight. DCM is evaporated. The residue is dissolved in EtOAc (20 mL), washed with water (5 mL×3) and brine, dried over sodium sulfate, and concentrated. The crude product is purified through PTLC to give the title compound. 1H NMR (300 MHz, CDCl3) δ 7.85 (2H, d), 6.85 (2H, d), 3.89 (2H, br), 3.66 (2H, t), 3.49 (2H, t), 2.91 (2H, dt), 2.46˜2.57 (8H, overlapped), 2.26 (2H, d), 2.12 (1H, m), 1.22˜1.95 (12H, m); LC-MS (M+1) 398.

Aufarbeitung

  1. customDCM is evaporated
  2. dissolutionThe residue is dissolved in EtOAc (20 mL)
  3. washwashed with water (5 mL×3) and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe crude product is purified through PTLC

Quellen und Nachweise

ORD-Eintrag
ord-560002b7921b493fa74d17edcb3fa32d
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07851474B2

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