Hydrochloric Acid → 2-{[2-(2-Chlorophenyl)ethyl](methyl)amino}ethan-1-ol

To 400 ml. of a 1 mol solution of borane in tetrahydrofuran was added dropwise a solution of 43 g. of the above amide in 350 ml. of tetrahydrofuran at a rate sufficient to maintain a gentle reflux. After addition was complete, the solution was refluxed for two hours, cooled in an ice bath and treated carefully with dilute hydrochloric acid to destroy excess borane. The majority of the solvent was removed under vacuum and the residue heated on a steam bath for one hour. The mixture was diluted with 300 ml. of water and extracted with ether. The aqueous layer was made basic with 40% sodium hydroxide and extracted with ether. The combined basic extracts were washed with water and saturated sodium chloride, dried and evaporated to give 2-[[2-(2-chlorophenyl)-ethyl]methylamino]ethanol.

1. additionAfter addition
2. temperaturethe solution was refluxed for two hours
3. temperaturecooled in an ice bath
4. customto destroy excess borane
5. customThe majority of the solvent was removed under vacuum
6. temperaturethe residue heated on a steam bath for one hour
7. additionThe mixture was diluted with 300 ml
8. extractionof water and extracted with ether
9. extractionextracted with ether
10. washThe combined basic extracts were washed with water and saturated sodium chloride
11. customdried
12. customevaporated

ORD record

ord-01355630b7724786979cfc04cee71dd0

Source dataset

uspto-grants-1984_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04465677