Hydrochloric Acid → 6-(p-Chlorophenyl)hexylamine

Temperature

0 °C

A solution of 16.4 g (0.073 mole) of 6-(p-chlorophenyl hexanamide (VI) in 30 ml. of dry tetrahydrofuran was added dropwise to a stirred solution of 170 ml of 1.0M diborane/tetrahydrofuran solution (Aldrich) at 0° C. under a nitrogen atmosphere. After addition, the mixture was stirred at 0° C. for 15 minutes, then warmed to reflux and kept there for 2.5 hours. The mixture was cooled to room temperature, and 85 ml of 6N hydrochloric acid was added cautiously to quench the reaction. The solvent was removed and the aqueous mixture was brought to pH 10 with 10% sodium hydroxide solution. The aqueous mixture was extracted three times with 60 ml portions of ethyl acetate. The combined ethyl acetate extracts were washed with saturated sodium chloride solution, dried over sodium sulfate, filtered, and evaporated leaving an oil. Distillation under reduced pressure afforded 10.4 g (67%) of VII as a colorless oil, bp. 108°-115° C. (0.3 torr).

1. additionAfter addition
2. temperaturewarmed
3. temperatureto reflux
4. waitkept there for 2.5 hours
5. temperatureThe mixture was cooled to room temperature
6. customto quench
7. customthe reaction
8. customThe solvent was removed
9. extractionThe aqueous mixture was extracted three times with 60 ml portions of ethyl acetate
10. washThe combined ethyl acetate extracts were washed with saturated sodium chloride solution
11. dry with materialdried over sodium sulfate
12. filtrationfiltered
13. customevaporated
14. customleaving an oil
15. distillationDistillation under reduced pressure

ORD record

ord-233ec9b50f324b59b31c60cf47e2b2f3

Source dataset

uspto-grants-1985_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04554276