Piperidine → 2-[6-(methylamino)pyridin-3-yl]-1,3-benzothiazol-6-ol

HRID 2276908Notes

Reaction equation

HRID 2276908 reaction equation
[CH3:1][NH:2][C:3]1C=[CH:7][C:6]([C:9]2[S:10][C:11]3[CH:17]=[C:16]([OH:18])[CH:15]=[CH:14][C:12]=3[N:13]=2)=[CH:5][CH:4]=1.O(C(OC(C)(C)C)=O)C(OC(C)(C)C)=O.[NH:34]1CCCCC1.[Cl-].[NH4+]>O1CCCC1>[CH3:1][NH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[S:10][C:11]3[CH:17]=[C:16]([OH:18])[CH:15]=[CH:14][C:12]=3[N:13]=2)=[CH:7][N:34]=1

Participants

6

Reactant 4

HCID 8082PiperidineHCID 25517Ammonium ChlorideHCID 90495Di-tert-butyl dicarbonateHCID 101714872-[4-(Methylamino)phenyl]-1,3-benzothiazol-6-ol

Product 1

HCID 166632752-[6-(methylamino)pyridin-3-yl]-1,3-benzothiazol-6-olYield 99.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-[4-(N-monomethyl)aminophenyl]-6-hydroxybenzothiazole (45, 520 mg, 2.03 mmol) was dissolved in tetrahydrofuran (15 mL) and (BOC)2O (974 mg, 4.46 mmol) and N,N-dimethylaminopyridine (DMAP; 496 mg, 4.06 mmol) were sequentially added thereto. After agitating the resulting reaction mixture for 16 hours at room temperature and removing the solvent under reduced pressure, the mixture was dissolved again in dichloromethane (40 mL). Then, after adding piperidine (4.0 mL, 40.6 mmol), the reaction mixture was agitated for 1 hour at room temperature and ammonium chloride aqueous solution was added. After extracting the organic compound with dichloromethane and removing water using sodium sulfate, column chromatography yielded the target compound 2-[2-(N-monomethylamino)pyridin-5-yl]-6-hydroxybenzothiazole (12-4, 519 mg, 72%) as a white solid.

Workup

  1. customthe resulting reaction mixture for 16 hours at room temperature
  2. customremoving the solvent under reduced pressure
  3. dissolutionthe mixture was dissolved again in dichloromethane (40 mL)
  4. stirringthe reaction mixture was agitated for 1 hour at room temperature
  5. extractionAfter extracting the organic compound with dichloromethane
  6. customremoving water

Sources & evidence

ORD record
ord-4c332d68c1d6434397fc08c166ecbfa9
Source dataset
uspto-grants-2015_09
Patent number
US09133143B2

Reaction notes

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