Triethylamine → 2-(3-Methylpiperazin-1-YL)aniline

温度

100 °C

2(R),5(S)-Dimethyl-1-N-benzyl-piperazine (6.0 g, 29 mmol) was dissolved in dimethylformamide (100 mL), and triethylamine (6.4 mL, 44 mmol) and the mixture was placed under nitrogen. To the solution was added 2-fluoro-nitrobenzene (3.5 mL, 31 mmol). The reaction was heated at 100° C. for 72 hours The solution was evaporated in vacuo and redissolved in ethyl acetate (100 mL). The solution was then washed with saturated sodium bicarbonate solution (100 mL) and saturated brine solution (100 mL). The separated organic phase was dried over magnesium sulfate, filtered and the filtrate was evaporated in vacuo. The crude product was then purified by flash chromatography, eluting with ethyl acetate/methanol/triethylamine 85:10:5. The product (8.2 g) was dissolved in ethanol (250 mL). Palladium on charcoal catalyst (10% w/w, 2.2 g) was added to the solution and the solution was hydrogenated in a Parr apparatus at 3 bar for 3 hours. The solution was filtered and evaporated to give the aniline product. Yield (5.2 g, 87%)

1. customwas evaporated in vacuo
2. dissolutionredissolved in ethyl acetate (100 mL)
3. washThe solution was then washed with saturated sodium bicarbonate solution (100 mL) and saturated brine solution (100 mL)
4. dry with materialThe separated organic phase was dried over magnesium sulfate
5. filtrationfiltered
6. customthe filtrate was evaporated in vacuo
7. customThe crude product was then purified by flash chromatography
8. washeluting with ethyl acetate/methanol/triethylamine 85:10:5
9. dissolutionThe product (8.2 g) was dissolved in ethanol (250 mL)
10. additionPalladium on charcoal catalyst (10% w/w, 2.2 g) was added to the solution
11. filtrationThe solution was filtered
12. customevaporated

ORDレコード

ord-cf3eec303899417097cc277456728ea1

出典データセット

uspto-grants-2006_06

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07067501B2