4-(1-(4-Bromophenyl)piperidin-4-yl)morpholine → 4-(4-Morpholinopiperidin-1-yl)phenylboronic acid

HRID 1466271Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1466271
C(N1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([B:16]([OH:18])[OH:17])=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)(C)C.BrC1C=CC(N2CC[CH:29]([N:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)CC2)=CC=1>>[O:35]1[CH2:36][CH2:37][N:32]([CH:29]2[CH2:5][CH2:6][N:7]([C:10]3[CH:11]=[CH:12][C:13]([B:16]([OH:17])[OH:18])=[CH:14][CH:15]=3)[CH2:8][CH2:9]2)[CH2:33][CH2:34]1

Komponenten

3

Edukt 2

HCID 667303494-(1-(4-Bromophenyl)piperidin-4-yl)morpholineHCID 66730443(4-(4-Isopropylpiperazin-1-yl)phenyl)boronic acid

Produkt 1

HCID 584862764-(4-Morpholinopiperidin-1-yl)phenylboronic acidAusbeute 40 %

Versuchsvorschrift

The title compound was synthesized according to the synthesis of 4-(4-isopropylpiperazin-1-yl)phenylboronic acid, except substituting 4-(1-(4-bromophenyl)piperidin-4-yl)morpholine (250 mg, 0.77 mmol). The aqueous layer was washed with EtOAc and concentrated. The residue was triturated with THF and the filtrate was concentrated to give the title compound as a yellow solid (87 mg, 40%). 1H NMR (400 MHz, MeOD) δ 7.58 (br s, 2H), 6.93 (d, J=7.5 Hz, 2H), 3.85-3.82 (m, 2H), 3.72 (br s, 4H), 2.72 (t, J=12.3 Hz, 2H), 2.63 (br s, 4H), 2.40-2.34 (m, 1H), 2.01-1.98 (m, 2H), 1.62-1.54 (m, 2H); MS ESI 291.1 [M+H]+, calcd for [C15H23BN2O3+H]+ 291.18.

Aufarbeitung

  1. customThe title compound was synthesized
  2. washThe aqueous layer was washed with EtOAc
  3. concentrationconcentrated
  4. customThe residue was triturated with THF
  5. concentrationthe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-39220e0fd6154325accd893fa29db694
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US08999968B2

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