Methyl iodide → 2-(4-Methoxyphenyl)-2-methylpropan-1-amine

To a solution of (4-methoxy-phenyl)-acetonitrile [5 g, 34 mmol] in THF (40 mL), is added a 1.5 M solution of lithium diisopropylamide in cyclohexane (36 mL, 54 mmol) at −78° C. After 2 hours at −78° C., methyl iodide (3.4 g, 54 mmol) is added, and the mixture is allowed to warm to room temperature over 3 hours. After additional 12 hours at 20° C., the mixture is diluted with aqueous ammonium chloride solution, and extracted with ethyl acetate. The extracts are dried over magnesium sulfate, filtered and concentrated. The residue is subjected to chromatography on silica gel eluting with 40% EtOAc in heptane to afford a mixture of 2-(4-ethoxy-phenyl)-propionitrile and 2-(4-methoxy-phenyl)-2-methyl-propionitrile. To above mixture (5 g) in THF (20 mL) is add a 2 M solution of lithium aluminum hydride (35 mL, 70 mmol) at 0° C. After 12 hours at 20° C., the mixture is carefully quenched with 10% sodium hydroxide solution, and the white slurry is diluted with ether. The mixture is dried over magnesium sulfate, filtered and concentrated. The residue is subjected to chromatography on silica to afford 2-(4-methoxy-phenyl)-2-methyl-propylamine [2 g, 33%, Intermediate (35)]. MS: 180 (M+H).

1. waitAfter additional 12 hours at 20° C.
2. extractionextracted with ethyl acetate
3. dry with materialThe extracts are dried over magnesium sulfate
4. filtrationfiltered
5. concentrationconcentrated
6. customto afford
7. waitAfter 12 hours at 20° C.
8. customthe mixture is carefully quenched with 10% sodium hydroxide solution
9. additionthe white slurry is diluted with ether
10. dry with materialThe mixture is dried over magnesium sulfate
11. filtrationfiltered
12. concentrationconcentrated

ORD 기록

ord-a2e8851f2c1d4f27b7ceaa176f8c7208

출처 데이터셋

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08193183B2