1-(4-Bromophenyl)-cis-3,5-dimethylpiperazine → 4-(cis-3,5-Dimethylpiperazin-1-yl)phenylboronic acid

HRID 447464Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 447464
C(N1CCN(C2C=CC([B:16]([OH:18])[OH:17])=CC=2)CC1)(C)C.Br[C:20]1[CH:25]=[CH:24][C:23]([N:26]2[CH2:31][C@H:30]([CH3:32])[NH:29][C@H:28]([CH3:33])[CH2:27]2)=[CH:22][CH:21]=1>>[CH3:33][C@H:28]1[NH:29][C@@H:30]([CH3:32])[CH2:31][N:26]([C:23]2[CH:24]=[CH:25][C:20]([B:16]([OH:18])[OH:17])=[CH:21][CH:22]=2)[CH2:27]1

Komponenten

3

Edukt 2

HCID 667303611-(4-Bromophenyl)-cis-3,5-dimethylpiperazineHCID 66730443(4-(4-Isopropylpiperazin-1-yl)phenyl)boronic acid

Produkt 1

HCID 584863454-(cis-3,5-Dimethylpiperazin-1-yl)phenylboronic acid

Versuchsvorschrift

The title compound was synthesized according to the synthesis of 4-(4-isopropylpiperazin-1-yl)phenylboronic acid, except substituting 1-(4-bromophenyl)-cis-3,5-dimethylpiperazine (300 mg, 1.11 mmol). The reaction was quenched with sat. NH4Cl solution, extracted with EtOAc, dried over MgSO4, filtered, and concentrated to dryness. The title compound was isolated by silica gel chromatography (MeOH/CH2Cl2, 6:94 to 1:4) as a yellow solid (59 mg, 23%). 1H NMR (400 MHz, MeOD) δ 7.59 (d, J=6.2 Hz, 2H), 6.91 (d, J=8.2 Hz, 2H), 3.67-3.63 (m, 2H), 3.09-3.01 (m, 2H), 2.32 (t, J=11.6 Hz, 2H), 1.18 (d, J=6.4 Hz, 6H); MS ESI 235.1 [M+H]+, calcd for [C12H19BN2O2+H]+ 235.15.

Aufarbeitung

  1. customThe title compound was synthesized
  2. customThe reaction was quenched with sat. NH4Cl solution
  3. extractionextracted with EtOAc
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-2eba2c37dc4845a3ad8dc3802f151512
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481525B2

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