Potassium Carbonate → HCID 68494469, compound

HRID 453885Notes

Reaction equation

[C:1]([O:5][C:6](=[O:11])[NH:7][CH2:8][CH2:9]Br)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH3:18][N:19]([CH3:31])[C:20]1([C:26]2[S:27][CH:28]=[CH:29][CH:30]=2)[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.CO.C(Cl)(Cl)Cl>C1COCC1>[CH3:18][N:19]([CH3:31])[C:20]1([C:26]2[S:27][CH:28]=[CH:29][CH:30]=2)[CH2:25][CH2:24][N:23]([CH2:9][CH2:8][NH:7][C:6](=[O:11])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:22][CH2:21]1

Participants

Conditions

Temperature: 70 °C

Procedure

11.1 g (1.5 eq.) tert-butyl-2-bromoethylcarbamate dissolved in 65 ml THF and 9.19 g (2 eq.) potassium carbonate were added to a solution of 7 g (1 eq.) N,N-dimethyl-4-(thiophen-2-yl)piperidin-4-amine in 40 ml THF. The reaction mixture was heated for 6 h at 70° C. The reaction course was monitored by thin-layer chromatography (20% MeOH/CHCl3). Once the conversion was complete, the solvent was distilled off completely, the residue mixed with 200 ml water and the aqueous phase extracted with 20% IPA/CHCl3. The combined organic phases were dried over Na2SO4. Following removal of the solvent under reduced pressure, the residue was purified by column chromatography (silica gel; 10% MeOH/CHCl3). 9 g (76%) of product were obtained in the form of an oil.

Workup

distillationthe solvent was distilled off completely
additionthe residue mixed with 200 ml water
extractionthe aqueous phase extracted with 20% IPA/CHCl3
dry with materialThe combined organic phases were dried over Na2SO4
customremoval of the solvent under reduced pressure
customthe residue was purified by column chromatography (silica gel; 10% MeOH/CHCl3)

Sources & evidence

ORD record: ord-c3d5420be44f4e40b0d0aa12c202f63b
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08492559B2

Reaction notes

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