N,N'-Dimethylthiourea → HCID 178482535, compound

HRID 493714Notes

Reaction equation

HRID 493714 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 68%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

tert-Butyl 4-(1-bromo-2-oxoethyl)piperidine-1-carboxylate (WO 0059502: 21.0 g) and a solution of N,N′-dimethylthiourea (6.0 g) in ethanol (300 mL) were heated under reflux. The reaction solution was concentrated, and the residue was dissolved in ethyl acetate and water. The aqueous layer was collected by separation. The aqueous layer was basified with an aqueous potassium carbonate solution, and extracted with chloroform. The extract was dried over anhydrous sodium sulfate, and then the solvent was distilled off to give the title compound (12.2 g) as a pale yellow solid.

Workup

  1. temperatureunder reflux
  2. concentrationThe reaction solution was concentrated
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. customThe 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

Sources & evidence

ORD record
ord-91c1347b8d0847ecaf8576c6b51b637c
Source dataset
uspto-grants-2009_05
Patent number
US07534887B2

Reaction notes

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