Sodium Iodide → HCID 15086293, compound

HRID 1460444Notes

Reaction equation

[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].[I-].[Na+].[F:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=2)=[C:22]2[CH2:27][CH2:26][N:25]([CH2:28][CH2:29]Cl)[CH2:24][CH2:23]2)=[CH:17][CH:16]=1>O1CCCC1>[C:3]([CH:2]([CH2:29][CH2:28][N:25]1[CH2:24][CH2:23][C:22](=[C:21]([C:18]2[CH:17]=[CH:16][C:15]([F:14])=[CH:20][CH:19]=2)[C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=2)[CH2:27][CH2:26]1)[C:1]([O:7][CH2:8][CH3:9])=[O:6])(=[O:4])[CH3:5]

Participants

Conditions

Temperature: 20 °C

Procedure

0.182 mol of ethyl acetoacetate is added at 0° C. to a suspension containing 0.182 mol of sodium hydride in 800 ml of tetrahydrofuran. The reaction medium is maintained for one hour at 20° C. and 0.182 mol of sodium iodide is then added. The mixture is cooled to 0° C. and 0.182 mol of 4-[bis(4-fluorophenyl)methylene]-1-(chloroethyl)piperidine is added. The mixture is brought to reflux for 12 hours and then concentrated under vacuum. The residue is taken up in water and the product is extracted with dichloromethane. The oil obtained is purified by chromatography on a column of 70-230 mesh silica, eluting with a mixture of dichloromethane and methanol (99:1 V/V).

Workup

temperatureThe mixture is cooled to 0° C.
temperatureto reflux for 12 hours
concentrationconcentrated under vacuum
extractionthe product is extracted with dichloromethane
customThe oil obtained
customis purified by chromatography on a column of 70-230 mesh silica
washeluting with a mixture of dichloromethane and methanol (99:1 V/V)

Sources & evidence

ORD record: ord-9c24300e6cb74680bf28d2aed57e3c95
Source dataset: uspto-grants-1991_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05071847

Reaction notes

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