Triethylamine → 8-(4-Benzyl-piperazin-1-yl)-6-bromo-quinoline

The free base of bis(2-chloroethyl)-benzlyamine (5.12 g, 19.3 mmol) was prepared by washing the HCl salt with 1 M NaOH (200 mL) and extracting into EtOAc. The resulting organic phases were dried over Na2SO4 and concentrated. To this flask was added 6-bromo-8-amino-quinoline (2.15 g, 9.6 mmol), n-BuOH (100 mL), and Et3N (4 mL, 28.9 mmol). The resulting reaction mixture was stirred at 100° C. overnight. TLC analysis showed starting amine was still present, therefore an additional portion of bis(2-chloroethyl)-benzylamine hydrochloride (5 g) was added. The reaction was heated an additional 72 hours. The cooled reaction mixture was quenched with 1 M NaOH (200 mL) and extracted into EtOAc (3×200 mL). The organic fractions were combined, dried over Na2SO4, and concentrated. The resulting gold oil was purified three times by column chromatography (40% EtOAc/hexanes) affording 1.2 g (33%) of a viscous orange oil which solidified upon standing: mp 65-68° C., MS (+) APCI m/z 382 [M+H]+.

1. customThe free base of bis(2-chloroethyl)-benzlyamine (5.12 g, 19.3 mmol) was prepared
2. washby washing the HCl salt with 1 M NaOH (200 mL)
3. extractionextracting into EtOAc
4. dry with materialThe resulting organic phases were dried over Na2SO4
5. concentrationconcentrated
6. customThe resulting reaction mixture
7. temperatureThe reaction was heated an additional 72 hours
8. customThe cooled reaction mixture
9. customwas quenched with 1 M NaOH (200 mL)
10. extractionextracted into EtOAc (3×200 mL)
11. dry with materialdried over Na2SO4
12. concentrationconcentrated
13. customThe resulting gold oil was purified three times by column chromatography (40% EtOAc/hexanes)

ORD 기록

ord-0aeb211d43af4706826087252b4e1414

출처 데이터셋

uspto-grants-2002_10

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US06465482B2