Potassium Carbonate → HCID 22939251, compound

HRID 2054318Notes

Reaction equation

[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][CH:15]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[NH:25][C:26](=[O:31])C(Cl)(Cl)Cl)[CH:16]([CH3:18])[CH3:17])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C.C1(C)C=CC=CC=1>CN(C)C=O>[CH:16]([CH:15]1[C:19]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[NH:25][C:26](=[O:31])[N:14]1[CH:11]1[CH2:10][CH2:9][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:13][CH2:12]1)([CH3:17])[CH3:18]

Participants

Conditions

Temperature: 90 °C

Procedure

Into a solution of 6.58 g (13.6 mmol) of 1-benzyl-4-[2-methyl-1-(2-trichloroacetylaminophenyl)propylamino]piperidine in 136 ml of dimethylformamide, 9.42 g (68 mmol) of potassium carbonate were added and stirred at 90° C. for 5 hours. The reaction mixture was cooled to room temperature, and then 0.5% aqueous potassium carbonate solution and ethyl acetate-toluene (1:1) were added thereto and stirred. The separated oil layer was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The concentrated residue was purified by silica gel column chromatography (chloroform/methanol 100/2) to give 3.65 g (10.0 mmol) of the above-titled compound.

Workup

temperatureThe reaction mixture was cooled to room temperature
stirringstirred
washThe separated oil layer was washed with saturated brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThe concentrated residue was purified by silica gel column chromatography (chloroform/methanol 100/2)

Sources & evidence

ORD record: ord-775a2a9c9d5f4ef188b186f5a1cba598
Source dataset: uspto-grants-2008_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07329665B2

Reaction notes

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