Trifluoroacetic acid → HCID 20313237, compound

To 50 ml. of anhydrous tetrahydrofuran was added 1g. (0.04 atom) of magnesium and then methyl bromide was added dropwise to the mixture at 5°-10° C. to provide a Grignard reagent. Then, a solution prepared by dissolving 2 g. (0.004 mole) of 2-(1-oxo-4-indanyloxymethyl)-4-triphenylmethyl morpholine in 20 ml. of anhydrous tetrahydrofuran was added dropwise to the reagent at 5°-10° C. Then, the mixture was stirred for 3 hours at room temperature and the solvent was distilled off under reduced pressure. The residue formed was mixed with saturated aqueous ammonium chloride solution and the mixture was extracted with chloroform. The extract obtained was washed with water, dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue formed was dissolved in 20 ml. off trifluoroacetic acid under ice-cooling and 20 ml. of water was immediately added to the solution followed by stirring for 15 minutes at 5°-10° C. The reaction mixture was neutralized with sodium hydrogencarbonate and extracted with chloroform. The extract was washed with water, dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. Thereafter, the residue formed was subjected to a silica gel column chromatography (diameter 3 cm., height 7 cm.) and from the fraction recovered therefrom using a 8 : 2 mixture of chloroform and methanol 820 mg. of sticky 2-(1-hydroxy-1-methyl-4-indanyloxymethyl)morpholine was obtained.

1. customThen, a solution prepared
2. dissolutionby dissolving 2 g
3. distillationthe solvent was distilled off under reduced pressure
4. customThe residue formed
5. extractionthe mixture was extracted with chloroform
6. customThe extract obtained
7. washwas washed with water
8. dry with materialdried over anhydrous magnesium sulfate
9. distillationthe solvent was distilled off under reduced pressure
10. customThe residue formed
11. dissolutionwas dissolved in 20 ml
12. stirringby stirring for 15 minutes at 5°-10° C
13. extractionextracted with chloroform
14. washThe extract was washed with water
15. dry with materialdried over anhydrous magnesium sulfate
16. distillationthe solvent was distilled off under reduced pressure
17. customThereafter, the residue formed
18. customrecovered
19. additiona 8 : 2 mixture of chloroform and methanol 820 mg

ORD record

ord-d34adc9013f842808b87f2c1ba07c6aa

Source dataset

uspto-grants-1978_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04109088