Ammonium Chloride → HCID 14770836, compound

HRID 1090373Notes

Reaction equation

Br[C:2]1[C:10]([F:11])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([F:12])[CH:3]=1.C([Li])CCC.[CH3:18][N:19]1[CH2:24][CH2:23][C:22](=[O:25])[CH2:21][CH2:20]1.[Cl-].[NH4+]>O1CCCC1.CCCCCC.O>[F:12][C:4]1[CH:3]=[C:2]([C:22]2([OH:25])[CH2:23][CH2:24][N:19]([CH3:18])[CH2:20][CH2:21]2)[C:10]([F:11])=[CH:9][C:5]=1[C:6]([OH:8])=[O:7]

Participants

Conditions

Temperature: -30 °C

Procedure

A solution of 1.19 g (5 mmoles) of 4-bromo-2,5-difluorobenzoic acid in 20 ml of tetrahydrofuran at -75° C. was treated with 4.2 ml of 2.4 M n-butyl lithium in hexane. The mixture was stirred 20 minutes, treated with a solution of 0.58 g (5.1 mmoles) of 1-methyl-4-piperidone in 5 ml tetrahydrofuran, stirred a further 1.5 hours, let warm to -30° C., and treated with a solution of 0.55 g (10.3 mmoles) ammonium chloride in 20 ml water. The product, the title compound, crystallized on standing.

Workup

stirringstirred a further 1.5 hours
customThe product, the title compound, crystallized

Sources & evidence

ORD record: ord-901ff4a53ce14fb5883936e73f0899d8
Source dataset: uspto-grants-1992_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05081254

Reaction notes

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