Iodine → HCID 23512834, compound

Temperature

0 °C

At 0° C., a solution of of 4-(4-chlorophenyl)-N-methylbutyramide (3.80 g, 18.0 mmol) in tetrahydrofuran (60 ml) was added to a suspension of sodium borohydride (1.60 g, 43.1 mmol) in THF (60 ml). The mixture was stirred for 20 min at 0° C. A solution of iodine (4.6 g, 18.0 mmol) in THF (100 ml) was added dropwise. After the addition was finished, the reaction mixture was warmed to 70° C. It was stirred for 16 hours at this temperature. It was cooled to 0° C. Methanol (100 ml) was added dropwise. The solvents were removed in vacuo. The residue was dissolved in a 20% aqueous solution of sodium hydroxide (160 ml) and tert-butyl methyl ether (200 ml). The phases were separated. The aqueous phase was extracted with tert-butyl methyl ether (3×70 ml). The combined organic layers were dried over magnesium sulphate. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (90 g), using DCM/methanol/25% aqueous ammonia as eluent, to give 820 mg of N-[4-(4-chlorophenyl)butyl]-N-methylamine.

1. additionAfter the addition
2. temperaturethe reaction mixture was warmed to 70° C
3. stirringIt was stirred for 16 hours at this temperature
4. temperatureIt was cooled to 0° C
5. customThe solvents were removed in vacuo
6. dissolutionThe residue was dissolved in a 20% aqueous solution of sodium hydroxide (160 ml) and tert-butyl methyl ether (200 ml)
7. customThe phases were separated
8. extractionThe aqueous phase was extracted with tert-butyl methyl ether (3×70 ml)
9. dry with materialThe combined organic layers were dried over magnesium sulphate
10. customThe solvent was removed in vacuo
11. customThe crude product was purified by flash chromatography on silica (90 g)

ORD record

ord-6ceb6c01435744528cc93bbaabd4decc

Source dataset

uspto-grants-2002_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06437147B1