Electric Literature of 954-81-4,Some common heterocyclic compound, 954-81-4, name is N-(5-Bromopentyl)phthalimide, molecular formula is C13H14BrNO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
A mixture of N-(5-bromopentyl)phthalimide (1.49 g, 5 mmol) and N,N-diisopropylethylamine (870 muL, 5 mmol) was dissolved in NMP (2 mL) followed by morpholine (870 muL, 5.5 mmol). The reaction mixture was stirred at room temperature overnight, the formed precipitate was filtered, and the filtrate evaporated. The crude product was triturated from EtOAc, filtered, and dried in vacuo to provide the alkylated morpholine intermediate (939 mg) as a white solid. The intermediate was dissolved in ethanol (20 mL) then treated with hydrazine hydrate (155 muL, 3.1 mmol). The reaction mixture was heated at reflux for 2 h, cooled to room temperature, and the formed precipitate was filtered. The filtrate was concentrated in vacuo, and the resulting residue was dissolved in chloroform (5 mL) followed by treatment with N-(9-fluorenylmethoxycarbonyl)-isothiocyanate (872 mg, 3.1 mmol) The reaction mixture was maintained at room temperature for 2 h, then concentrated in vacuo. The resulting oil was dissolved in EtOAc (5 mL), treated with piperidine (614 muL, 6.2 mmol), stirred at room temperature for 30 min, and concentrated in vacuo. The resulting residue was dissolved in dichloromethane (10 mL), and the formed precipitate was filtered and dried in vacuo to provide 1-(5-morpholinopentyl)thiourea (287 mg, 58%) as a yellowish amorphous solid.
The synthetic route of 954-81-4 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; Dickson, John K.; Hodge, Carl Nicholas; Mendoza, Jose Serafin; Chen, Ke; US2006/52416; (2006); A1;,
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