Hydrogen Bromide → 2-[4-[2-[2-(4-Pyridyl)piperazin-1-yl]acetyl]phenoxy]-isobutyric acid, dihydrobromide

HRID 2216

Reaction equation

N1C=CC([N:7]2[CH2:12][CH2:11][N:10]([CH2:13][C:14]([C:16]3[CH:29]=[CH:28][C:19]([O:20][C:21]([CH3:27])([CH3:26])[C:22]([O:24]C)=[O:23])=[CH:18][CH:17]=3)=[O:15])[CH2:9][CH2:8]2)=CC=1.[BrH:30].O1[CH2:36][CH2:35]OCC1>O>[BrH:30].[BrH:30].[N:10]1[CH:36]=[CH:35][C:16]([CH:9]2[CH2:8][NH:7][CH2:12][CH2:11][N:10]2[CH2:13][C:14]([C:16]2[CH:29]=[CH:28][C:19]([O:20][C:21]([CH3:27])([CH3:26])[C:22]([OH:24])=[O:23])=[CH:18][CH:17]=2)=[O:15])=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 95 °C

Procedure

A mixture of methyl 2-[4-[2-[4-(4-pyridyl)piperazin-1-yl]-acetyl]phenoxy]isobutyrate (50 mg), 48% w/v hydrobromic acid (0.74 ml), dioxane (1 ml) and water (3 ml) was heated at 95° C. for 4 hours. The solution was cooled, diluted with water and freeze-dried to give the title compound, 40 mg, as a pale yellow solid: m.p. 163°-167° C.; NMR (D2O) δ 8.40 (2H, d), 8.16 (2H, d), 7.40 (2H, d), 7.21 (2H, d), 5.21 (2H, s), 4.32 (4H, b), 3.89 (4H, bt), 1.86 (6H, s); m/e 384 (M+H)+ ; calculated for C21H25N3.2HBr.2H2O: C, 43.3; H, 5.3; N, 7.2. found: C, 43.6; H, 5.3; N, 7.3%.

Workup

temperatureThe solution was cooled
customfreeze-dried

Sources & evidence

ORD record: ord-76266dbb7ecd40f78d7b97f8f4934f98
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05728701

Linked notes

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