Sodium Hydroxide → 1-(2-Benzothiazolylthio)-3-methyl-piperidine

HRID 25894

Reaction equation

HRID 25894 reaction equation
[SH:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[OH-].[Na+].[CH3:13][CH:14]1[CH2:19][CH2:18][CH2:17][NH:16][CH2:15]1.Cl[O-].[Na+]>C(OCC)(=O)C.O>[S:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=[C:2]1[S:1][N:16]1[CH2:17][CH2:18][CH2:19][CH:14]([CH3:13])[CH2:15]1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 790813-MethylpiperidineHCID 23665760Sodium HypochloriteHCID 178418395HCID 178418395, compound

Product 1

HCID 213256691-(2-Benzothiazolylthio)-3-methyl-piperidineYield 95.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a 500 ml volume flask, there are charged 2-mercaptobenzothiazole (UV absorption spectrum: 329 mμ) (41.28 g), sodium hydroxide (10 g) and water (180 ml), and the resultant mixture is stirred to form a solution. After the addition of 3-methylpiperidine (27.2 g) to the resulting solution, a 15 % by volume aqueous solution of sodium hypochlorite (138.5 ml) is dropwise added thereto in 2 hours, during which the inner temperature is kept below 70° C. The reaction mixture is allowed to stand at the same temperature for 1 hour and then shaken with ethyl acetate (150 ml). The ethyl acetate extract is washed with water and distilled under reduced pressure to give 1-(2-benzothiazolylthio)-3-methyl-piperidine (62.3 g).

Workup

  1. customto form a solution
  2. customis kept below 70° C
  3. waitto stand at the same temperature for 1 hour
  4. extractionThe ethyl acetate extract
  5. washis washed with water
  6. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-365611d060fb4b2cbbb7eaf6a8fdb453
Source dataset
uspto-grants-1979_04
Patent number
US04147696

Linked notes

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