Reaction #2122513

Reaction equation

Compound 2

2-methylbenzothiazole-6-sulfonyl chloride

piperidine

hexane

→

Compound 3

Yield 74.2%

N-(2-methylbenzothiazole-6-sulfonyl)piperidine

Yield 74.2%

Solvents

ethyl acetate

chloroform

chloroform

Conditions

Workup

1. 1
   WashThe reaction mixture was then washed with water (2×, 50 ml) and brine (1×, 50 ml)
2. 2
   DryingThe organic layer was dried with sodium sulfate
3. 3
   Otherevaporated
4. 4
   OtherThe sticky white solid thus obtained
5. 5
   OtherThe white solid that precipitated
6. 6
   Otherwas collected
7. 7
   Washwashed with hexane
8. 8
   Otherdried

Procedure

A solution of Compound 2 (2.5 g, 10 mmol) in chloroform (15 ml) was added drop wise to a solution of piperidine (1.7 g, 20.0 mmol) in chloroform (10 ml). The combined mixture was stirred at room temperature for 1 hour. The reaction mixture was then washed with water (2×, 50 ml) and brine (1×, 50 ml). The organic layer was dried with sodium sulfate and evaporated. The sticky white solid thus obtained was dissolved in ca. 5 ml of hot ethyl acetate and this solution was then slowly added to 40 ml hexane. The white solid that precipitated was collected, washed with hexane and dried to yield 2.2 g (74%) of Compound 3, Rf=0.28 (30% ethyl acetate in hexane). The structure of Compound 3 is given below:

Source