Iodine → N-Methyl-3-phenylpropan-1-amine

Temperatur

7 °C

N-(3-Phenylpropyl)formamide (5.70 g, 34.9 mmol) was dissolved in tetrahydrofuran (50 ml) and added dropwise to a suspension of sodium borohydride (1.58 g, 41.91 mmol) in tetrahydrofuran (100 ml), which was cooled to 7° C. A solution of iodine (4.42 g, 17.46 mmol) in tetrahydrofuran was added dropwise, while the temperature was kept at 7° C. After the addition was finished, the reaction mixture was warmed to reflux for 16 h. The reaction mixture was cooled to 7° C., and methanol (250 ml) was added dropwise. The solvent was removed in vacuo. The residue was dissolved in 20% aqueous sodium hydroxide solution (250 ml) and tert-butyl methyl ether (100 ml). The phases were separated. The aqueous phase was extracted with tert-butyl methyl ether (2×100 ml). The combined organic layers were dried over magnesium sulfate. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (400 g), using dichicromethane/methanol/25% aqueous ammonia (100:10:1) as eluent to give 2.76 g of N-methyl-N-(3-phenylpropyl)amine.

1. customwas kept at 7° C
2. additionAfter the addition
3. temperaturethe reaction mixture was warmed
4. temperatureto reflux for 16 h
5. temperatureThe reaction mixture was cooled to 7° C.
6. customThe solvent was removed in vacuo
7. dissolutionThe residue was dissolved in 20% aqueous sodium hydroxide solution (250 ml)
8. customThe phases were separated
9. extractionThe aqueous phase was extracted with tert-butyl methyl ether (2×100 ml)
10. dry with materialThe combined organic layers were dried over magnesium sulfate
11. customThe solvent was removed in vacuo
12. customThe crude product was purified by flash chromatography on silica (400 g)

ORD-Eintrag

ord-2b95b98d15cd46cfa6b107d261dde89f

Quelldatensatz

uspto-grants-2001_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06274584B1