Iodoethane → HCID 58878511, compound

HRID 1441668Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[O:25])[NH:15][C:16]2[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:17]=2[Br:24])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:28](I)[CH3:29]>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14](=[O:25])[N:15]([C:16]2[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:17]=2[Br:24])[CH2:28][CH3:29])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

4-(2-Bromo-5-methoxy-phenylcarbamoyl)-piperidine-1-carboxylic acid tert-butyl ester (0.5 g, 1.21 mmol) was dissolved in dry N,N-dimethylformamide (5.0 mL). To the reaction mixture was then added at 0° C. sodium hydride (60% in mineral oil, 60.0 mg, 1.45 mmol) under nitrogen atmosphere and the reaction mixture was stirred at 0° C. for one hour. To the reaction mixture was then added at 0° C., ethyl iodide (0.226 g, 1.45 mmol). The reaction mixture was stirred at 0° C. for one hour, then at room temperature under nitrogen atmosphere for 18 hours. The reaction mixture was then added into an excess of water-ice and a solid precipitated. The solid was filtered by suction, washed with water and dried to yield a crude solid. The crude solid was purified via flash chromatography (25% ethyl acetate/hexanes) to yield the title compound as a solid.

Workup

additionTo the reaction mixture was then added at 0° C.
stirringThe reaction mixture was stirred at 0° C. for one hour
waitat room temperature under nitrogen atmosphere for 18 hours
customa solid precipitated
filtrationThe solid was filtered by suction
washwashed with water
customdried
customto yield a crude solid
customThe crude solid was purified via flash chromatography (25% ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-b6b578ee66eb436188e41a10dbccfcc2
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07655670B2

Reaction notes

Loading…