Potassium Carbonate → Tert-butyl 4-(4-aminophenylthio)piperidine-1-carboxylate

HRID 624277Notes

Reaction equation

HRID 624277 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].S(O[CH:26]1[CH2:31][CH2:30][N:29]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:28][CH2:27]1)(C1C=CC(C)=CC=1)(=O)=O>CN(C)C=O>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH:26]2[CH2:31][CH2:30][N:29]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:28][CH2:27]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 145104-AminothiophenolHCID 157347131-(tert-Butoxycarbonyl)-4-(p-toluenesulfonyloxy)piperidine

Product 1

HCID 18538812Tert-butyl 4-(4-aminophenylthio)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a 100 mL round-bottomed flask was added 4-aminobenzenethiol (4.9 g, 39.1 mmol) and potassium carbonate (9.72 g, 70.3 mmol) in dimethylformamide (20 ml). tert-Butyl 4-(tosyloxy)piperidine-1-carboxylate (5 g, 14.07 mmol) was added and the reaction was stirred in a sealed flask at 70° C. for 20 hours. The mixture was cooled and filtered through a plug of silica gel with dichloromethane. The filtrate was concentrated under vacuum and chromatographed to give the title compound.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered through a plug of silica gel with dichloromethane
  3. concentrationThe filtrate was concentrated under vacuum
  4. customchromatographed

Sources & evidence

ORD record
ord-3a68db8cab6c47188cc5e39052ef622e
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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