Toluene → HCID 13653525, compound

To 250 ml of a 1:1 mixture of toluene:tetrahydrofuran, 35.0 gm N-(n-propyl)-4-t-butylphenoxyacetamide, the product of Example 16, was added. The resulting mixture was heated to reflux and then 42.8 ml borane methylsulfide was added slowly. The reaction mixture was maintained at reflux for 48 hours at which time completion of the reaction was checked by IR spectroscopy. The reaction mixture was then cooled and 200 ml methanol was added slowly to the system. The system was then acidified by bubbling hydrogen chloride gas through it, and then heated to reflux and refluxed for 1 hour. The solvent was removed by stripping; the resulting oil was redissolved in methanol and the methanol stripped. The residue was dissolved in methylene chloride and basified with sodium hydroxide. The methylene chloride solution was then washed with water. The methylene chloride was stripped to give 31.2 gm of the N-(n-propyl)ethanolamine 4-t-butylphenylether.

1. temperatureThe resulting mixture was heated
2. temperatureto reflux
3. temperatureThe reaction mixture was maintained
4. temperatureat reflux for 48 hours at which time completion of the reaction
5. temperatureThe reaction mixture was then cooled
6. customby bubbling hydrogen chloride gas through it
7. temperatureheated
8. temperatureto reflux
9. temperaturerefluxed for 1 hour
10. customThe solvent was removed by stripping
11. dissolutionthe resulting oil was redissolved in methanol
12. dissolutionThe residue was dissolved in methylene chloride and basified with sodium hydroxide
13. washThe methylene chloride solution was then washed with water

ORD record

ord-e5829f15418e411da203f48d08f9627a

Source dataset

uspto-grants-1986_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04588735