2-piperidinobenzothiazole synthesis

9synthesis methods

Product Name:2-piperidinobenzothiazole
CAS Number:2851-08-3
Molecular formula:C12H14N2S
Molecular Weight:218.32

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Yield:2851-08-3 174 mg

Reaction Conditions:

with oxygen;copper(II) bis(trifluoromethanesulfonate) in toluene; for 12 h;Reflux;

Steps:

4.2 General procedure for preparation of substituted 2-morpholinobenzo[d]thiazoles from substituted N-(phenyl) morpholine-4-carbothioamide using Cu(OTf)₂ (1-10)

General procedure: Substituted phenyl isothiocyanate (1-10) (1.5mmol) was treated with morpholine a (1.5mmol) under neat condition and instant formation of the corresponding thiourea was observed. To this in situ generated thiourea toluene (2mL) was added and medium was stirred at room temperature for 5min followed by the addition of copper triflate (10mol%). After that the reaction mixture was subjected to reflux in a preheated oil bath at 110°C under O₂ atmosphere. The progress of the reaction was monitored by TLC. After the completion of the reaction as judged from TLC the reaction mixture was cooled and then admixed with water (1mL) and the product was extracted with ethyl acetate (2×10mL). The organic layer was dried over anhydrous sodium sulfate (Na₂SO₄), filtered and evaporated under reduced pressure. The crude products so obtained were further purified through silica gel column chromatograph (hexane/ethyl acetate, 9:1) to yield the pure substituted 2-morpholinobenzo[d]thiazole (1a′-10a′). The identity and purity of the product was further confirmed by spectroscopic analysis. Reaction performed with phenyl isothiocyanate (1) (1.5mmol) and other secondary amines (b-f) (1.5mmol) in the above mentioned method and corresponding benzo[d]thiazoles (1b′-f′) were isolated and spectroscopically characterized.

References:

Banerjee, Arghya;Santra, Sourav Kumar;Rout, Saroj Kumar;Patel, Bhisma K. [Tetrahedron,2013,vol. 69,# 43,p. 9096 - 9104]