Sodium Hydroxide → 4-[3-(4-Cyclopropyl-piperazin-1-yl)-propoxy]-3-fluoro-benzoic Acid

HRID 220870Notes

Reaction equation

C([O:3][C:4](=[O:25])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][N:18]([CH:21]3[CH2:23][CH2:22]3)[CH2:17][CH2:16]2)=[C:7]([F:24])[CH:6]=1)C.[OH-].[Na+]>O1CCOCC1>[CH:21]1([N:18]2[CH2:17][CH2:16][N:15]([CH2:14][CH2:13][CH2:12][O:11][C:8]3[CH:9]=[CH:10][C:5]([C:4]([OH:25])=[O:3])=[CH:6][C:7]=3[F:24])[CH2:20][CH2:19]2)[CH2:23][CH2:22]1

Participants

Conditions

Temperature: 60 °C

Procedure

4-[3-(4-Cyclopropyl-piperazin-1-yl)-propoxy]-3-fluoro-benzoic acid ethyl ester from Example E48.2 (1.0 g, 2.9 mmol) was dissolved in dioxan (10 ml) and 2N NaOH solution (3 ml, 6.0 mmol) was added. The mixture was heated at 60° C. for 18 h then concentrated in vacuo. The residue was purified by flash chromatography on silica gel (eluant; 1% 35% ammonia:19% methanol:80% dichloro-methane) to yield the title compound (920 mg, 100%).

Workup

concentrationthen concentrated in vacuo
customThe residue was purified by flash chromatography on silica gel (eluant; 1% 35% ammonia:19% methanol:80% dichloro-methane)

Sources & evidence

ORD record: ord-e429b9689f244d9da72c6cabadf57d2f
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08202858B2

Reaction notes

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