Water → 5-(4-Ethylphenyl)-1-(morpholin-4-ylcarbonyl)-N-(prop-2-yn-1-yl)piperidine-3-carboxamide

HRID 1642856Notes

Reaction equation

[CH2:1]([NH2:4])[C:2]#[CH:3].C(N(CC)CC)C.[CH2:12]([C:14]1[CH:19]=[CH:18][C:17]([CH:20]2[CH2:25][N:24]([C:26]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)=[O:27])[CH2:23][CH:22]([C:34](Cl)=[O:35])[CH2:21]2)=[CH:16][CH:15]=1)[CH3:13].O>ClCCl>[CH2:12]([C:14]1[CH:19]=[CH:18][C:17]([CH:20]2[CH2:25][N:24]([C:26]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)=[O:27])[CH2:23][CH:22]([C:34]([NH:4][CH2:1][C:2]#[CH:3])=[O:35])[CH2:21]2)=[CH:16][CH:15]=1)[CH3:13]

Participants

Conditions

Temperature: 0 °C

Procedure

18 μl (16 mg, 0.29 mmol) of propargylamine, 40 μl (29 mg, 0.29 mmol) of triethylamine and 1 mg (0.01 mmol) of N,N-dimethylaminopyridine were initially charged in 0.5 ml of dichloromethane, and 105 mg (0.29 mmol) of 5-(4-ethylphenyl)-1-(morpholin-4-ylcarbonyl)piperidine-3-carbonyl chloride, dissolved in 1 ml of dichloromethane, were added. The reaction mixture was stirred at 0° C. for 30 minutes and at RT for 16 h. For work-up, water was added and the reaction mixture was extracted with ethyl acetate. The combined organic extracts were dried over magnesium sulphate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (mobile phase dichloromethane/methanol 100:5). Yield: 108 mg (98% of theory.)

Workup

additionwere added
extractionthe reaction mixture was extracted with ethyl acetate
dry with materialThe combined organic extracts were dried over magnesium sulphate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified by column chromatography on silica gel (mobile phase dichloromethane/methanol 100:5)

Sources & evidence

ORD record: ord-80ef1a578c7c45eca78e278d0f0d0fee
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08119663B2

Reaction notes

Loading…