Sodium hydride → HCID 18432931, compound

Temperature

0 °C

To a 0° C. suspension of NaH (0.11 g, 2.5 mmol, 55% in mineral oil) in DMF (3 ml) was added dropwise a DMF solution (3 ml) of a mixture of (2RS,5RS) and (2RS,5SR) (3-methyl-2-phenyl-oxazolidin-5-yl)-methanol (0.46 g, 2.4 mmol) in DMF (3 ml). After 15 min. at 0° C. and 2 hours at room temperature, reaction mixture was cooled to 0° C. and treated with a solution of 4-chloro-7-methyl-2-phenyl-quinoline (0.3 g, 1.2 mmol) in DMF (3 ml). After 5 min. at 0° C. and 21 hours at room temperature, the reaction mixture was cooled to 0° C., quenched with H2O (0.5 ml), and concentrated. The residue was treated with 1N HCl (6 ml). The so obtained yellow aqueous solution was extracted with CH2Cl2 (3×20 ml). Organic phases were washed with 1N HCl (2×10 ml). Combined aqueous phases were basified to pH 11 with 2N NaOH, and extracted with CH2Cl2 (3×20 ml). Combined organic phases were dried over Na2SO4 and concentrated. The residue was crystallized with Et2O to provide after filtration 95 mg of a white solid which was dissolved in MeOH. HCl-Et2O was added to provide (RS)-1-methylamino-3-(7-methyl-2-phenyl-quinolin-4-yloxy)-propan-2-ol hydrochloride (0.075 g, 16%) as a white solid, MS: m/e=323.3 (M+H+).

1. additionwas added dropwise
2. custom2 hours at room temperature, reaction mixture
3. waitAfter 5 min. at 0° C.
4. temperature21 hours at room temperature, the reaction mixture was cooled to 0° C.
5. customquenched with H2O (0.5 ml)
6. concentrationconcentrated
7. additionThe residue was treated with 1N HCl (6 ml)
8. customThe so obtained yellow aqueous solution
9. extractionwas extracted with CH2Cl2 (3×20 ml)
10. washOrganic phases were washed with 1N HCl (2×10 ml)
11. extractionextracted with CH2Cl2 (3×20 ml)
12. dry with materialCombined organic phases were dried over Na2SO4
13. concentrationconcentrated
14. customThe residue was crystallized with Et2O
15. customto provide
16. filtrationafter filtration 95 mg of a white solid which
17. dissolutionwas dissolved in MeOH
18. additionHCl-Et2O was added

ORD record

ord-50c48bd3dbff4dbcbacfda0201f5cf0f

Source dataset

uspto-grants-2002_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06440995B1