Water → 1-[4-(2-Chloro-4-fluoro-benzoyl)-piperidin-1-yl]-ethanone

HRID 1961643Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1I.C([Mg]Cl)(C)C.[Cl-].[Li+].[C:17]([N:20]1[CH2:28][CH2:27][CH:23]([C:24](Cl)=[O:25])[CH2:22][CH2:21]1)(=[O:19])[CH3:18].O>C1COCC1.CCCCCCC.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:24]([CH:23]1[CH2:22][CH2:21][N:20]([C:17](=[O:19])[CH3:18])[CH2:28][CH2:27]1)=[O:25]

Participants

Conditions

Temperature: 0 °C

Procedure

2-Chloro-4-fluoro-1-iodobenzol (5 g, 19 mmol) is solved in THF (3 mL) and at −10° C. isopropyl magnesium chloride-lithium chloride (2M in THF) was added dropwise and the mixture stirred for 30 minutes at 0° C. At −10° C. 1-acetyl-isonipecotoyl chloride is added (3.3 g, 18 mmol) solved in THF (2 mL) and the mixture stirred for 10 minutes to −10° C. and 4 h to 0° C. Water was added and the reaction extracted with dichloromethane. Chromatography with Heptane/EtOAc (2:1) gave the desired compound as a clear orange liquid (1.8 g, 33% yield). (m/e): 284.3 (M+H+).

Workup

additionwas added dropwise
customAt −10° C
stirringthe mixture stirred for 10 minutes to −10° C. and 4 h to 0° C
extractionthe reaction extracted with dichloromethane

Sources & evidence

ORD record: ord-539bb90652f846f3b0418fd6701a7881
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415350B2

Reaction notes

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