1-Methylpiperazine → (4-Methylpiperazin-1-yl){4-[(trimethylsilyl)ethynyl]phenyl}methanone

HRID 1403193

Reaktionsgleichung

Reaktionsgleichung von HRID 1403193
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[CH3:30][Si:31]([C:34]#[C:35][C:36]1[CH:44]=[CH:43][C:39]([C:40](O)=[O:41])=[CH:38][CH:37]=1)([CH3:33])[CH3:32]>C(Cl)Cl>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:40]([C:39]2[CH:43]=[CH:44][C:36]([C:35]#[C:34][Si:31]([CH3:30])([CH3:33])[CH3:32])=[CH:37][CH:38]=2)=[O:41])[CH2:4][CH2:3]1

Komponenten

6

Edukt 4

HCID 531671-MethylpiperazineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 136281904-[(Trimethylsilyl)ethynyl]benzoic acid

Produkt 1

HCID 71239568(4-Methylpiperazin-1-yl){4-[(trimethylsilyl)ethynyl]phenyl}methanoneAusbeute 93,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1-Methylpiperazine (0.66 mL, 6.0 mmol), HOBt (0.84 g, 6.2 mmol) and EDCl (1.15 g, 6.0 mmol) were added to a solution of 4-[(trimethylsilyl)ethynyl]benzoic acid (1.0 g, 4.6 mmol) in dry DCM (45 mL). The mixture was stirred at room temperature for 4 h, washed with saturated aqueous sodium bicarbonate (30 mL), brine, dried over sodium sulphate, and evaporated. The crude was purified by flash chromatography on silica gel (DCM/MeOH 96/4) to afford the title compound (1.29 g, 93%).

Aufarbeitung

  1. washwashed with saturated aqueous sodium bicarbonate (30 mL), brine
  2. dry with materialdried over sodium sulphate
  3. customevaporated
  4. customThe crude was purified by flash chromatography on silica gel (DCM/MeOH 96/4)

Quellen und Nachweise

ORD-Eintrag
ord-dee5acb81e2e4641a78d4ca58c28f42c
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08912200B2

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