Bromide ion → HCID 14856155, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2,2-dimethyl-3-(4-bromobutyl)-4-thiazolidinone (4.01 g), 1-(3-methylphenyl)piperazine (3.17 g), K2CO3 (5.30 g), NaI (230 mg) and CH3CN (180 mL) was heated at reflux (oil bath temperature; 100° C.) for 20 h. TLC analysis (silica gel, 7.5% EtOH/CH2 Cl2 showed one major product, Rf =0.53, and a trace of starting bromide, Rf =0.70. The reaction mixture was cooled to room temperature, EtOAc (100 mL) was added and the mixture filtered. The filtrate was concentrated in vacuo to an oil which was triturated with EtOAc (150 mL). The mixture was filtered and the filtrate concentrated in vacuo to an oil. HPLC of the crude oil (Waters Prep 500 silica gel, 8% MeOH/EtOAc) yielded 5.42 g of an oil, Rf =0.53. The hydrochloride salt of this amine was precipitated by the addition of HCl/Et2O to a solution of the base in 600 ml of ether until pH=2 to give 5.30 g of a white powder. Recrystallization from EtOH yielded 2.91 g of white crystals, mp 204° C. (dec).

Provenance & Evidence