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

HRID 2281731Notes

Reaction equation

HRID 2281731 reaction equation
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

Participants

3

Reactant 2

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

Product 1

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

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-70795a74353c41b6a5d0f0e030a7119c
Source dataset
uspto-grants-2015_09
Patent number
US09139563B2

Reaction notes

Loading…