Benzoyl isothiocyanate → 1,1-Dimethylethyl 4-(2-thiazolylamino)-1-piperidinecarboxylate

HRID 1162362Notes

Reaction equation

HRID 1162362 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH2:14])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:15]([N:23]=[C:24]=[S:25])(=O)[C:16]1C=CC=CC=1>C1COCC1>[S:25]1[CH:16]=[CH:15][N:23]=[C:24]1[NH:14][CH:11]1[CH2:12][CH2:13][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 12682914-Amino-1-Boc-piperidine

Product 1

HCID 231309421,1-Dimethylethyl 4-(2-thiazolylamino)-1-piperidinecarboxylateYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-Boc-4-aminopiperidine (6.0 g) in THF (100 ml) was added benzoyl isothiocyanate (4.1 ml), and mixed for 2 hours. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in methanol, potassium carbonate was added thereto, and mixed at 50° C. for 1 hour. The reaction mixture was concentrated under reduced pressure, and then the residue was dissolved in ethyl acetate. The mixture was washed with 1 N hydrochloric acid, a saturated aqueous sodium hydrogen carbonate solution and saturated brine. The ethyl acetate solution was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain the title compound as a pale yellow solid (7.3 g, 94%).

Workup

  1. additionmixed for 2 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in methanol
  4. additionpotassium carbonate was added
  5. additionmixed at 50° C. for 1 hour
  6. concentrationThe reaction mixture was concentrated under reduced pressure
  7. dissolutionthe residue was dissolved in ethyl acetate
  8. washThe mixture was washed with 1 N hydrochloric acid
  9. dry with materialThe ethyl acetate solution was dried over anhydrous sodium sulfate
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-aaf999b68a124443b2e94be93d30efb1
Source dataset
uspto-grants-2010_10
Patent number
US07820673B2

Reaction notes

Loading…