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

HRID 1466271Notes

Reaction equation

HRID 1466271 reaction equation
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

Participants

3

Reactant 2

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

Product 1

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

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-39220e0fd6154325accd893fa29db694
Source dataset
uspto-grants-2015_04
Patent number
US08999968B2

Reaction notes

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