N,N'-Dimethylthiourea → HCID 178482535, compound

HRID 1162364Notes

Reaction equation

HRID 1162364 reaction equation
Br[CH:2]([CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1)[CH:3]=O.[CH3:18][NH:19][C:20]([NH:22][CH3:23])=[S:21]>C(O)C>[CH3:23][N:22]1[CH:3]=[C:2]([CH:5]2[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]2)[S:21]/[C:20]/1=[N:19]\[CH3:18]

Participants

4

Reactant 2

HCID 2723631N,N'-DimethylthioureaHCID 21912701tert-Butyl 4-(1-bromo-2-oxoethyl)piperidine-1-carboxylate

Product 1

HCID 178482535HCID 178482535, compoundYield 66.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of tert-butyl 4-(1-bromo-2-oxoethyl)-1-piperidinecarboxylate (21 g) and N,N′-dimethylthiourea (6.0 g) in ethanol (300 ml) was heated under reflux. The reaction mixture was concentrated under reduced pressure, the residue was dissolved in ethyl acetate and water, and the aqueous layer was collected by separation. The residue was basified with an aqueous potassium carbonate solution and extracted with chloroform. The extract was dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure to obtain the title compound as a pale yellow solid (12 g, 57%).

Workup

  1. temperatureunder reflux
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. customwater, and the aqueous layer was collected by separation
  5. extractionextracted with chloroform
  6. dry with materialThe extract was dried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-482a37c0adcf46498db5e594ec78e44a
Source dataset
uspto-grants-2010_10
Patent number
US07820673B2

Reaction notes

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