Sodium Iodide → Ethyl 2-acetyl-4-[4-(4-fluorobenzoyl)piperidino]-butyrate

HRID 1461739Notes

Reaction equation

[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].[I-].[Na+].Cl[CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][CH:20]([C:23](=[O:31])[C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[CH2:19][CH2:18]1>O1CCCC1>[C:3]([CH:2]([CH2:15][CH2:16][N:17]1[CH2:18][CH2:19][CH:20]([C:23](=[O:31])[C:24]2[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=2)[CH2:21][CH2:22]1)[C:1]([O:7][CH2:8][CH3:9])=[O:6])(=[O:4])[CH3:5]

Participants

Conditions

Temperature: 20 °C

Procedure

A solution of 5.45 g of ethyl acetoacetate in 20 ml of tetrahydrofuran is added at 0° C. to a suspension of 1.68 g of sodium hydride at a concentration of 60% in oil in 100 ml of anhydrous tetrahydrofuran. The medium is maintained at 20° C. for 1 hour 30 minutes. 6.3 g of sodium iodide are added, followed by the addition at 0° C. of 11.3 g of 1-(2-chloroethyl)-4-(4-fluorobenzoyl)piperidine in 100 ml of tetrahydrofuran. The reaction mixture is brought to reflux for 15 hours. It is concentrated under vacuum. The residue is taken up in water and the product is extracted with dichloromethane.

Workup

temperatureto reflux for 15 hours
concentrationIt is concentrated under vacuum
extractionthe product is extracted with dichloromethane

Sources & evidence

ORD record: ord-eb99b06868674e2c9d29b38620f253b3
Source dataset: uspto-grants-1991_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05077288

Reaction notes

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