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

HRID 1466280Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1466280
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-df968fdb18724e7b944a60e51c65f975
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US08999968B2

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