Hydrochloric Acid → HCID 22735815, compound

Temperature

23 °C

To a 1.0 M THF solution of LiAlH4 (2.3 mL, 2.3 mmol) cooled to ˜10° C. was added dropwise via cannula over 3 min (internal temperature <25° C.) a THF solution (2.3 mL) of 9-methyl-5-nitroso-2,3,4,5-tetrahydro-1,5-benzothiazepine (crude, 470 mg, 2.3 mmol). The cooling bath was removed once the addition was finished, and the reaction was maintained at 25° C. to 32° C. for 1.5 h. H2O (0.1 mL) was added cautiously over 5 min, followed by THF (40 mL), aqueous NaOH solution (15%, 0.1 mL), and again H2O (0.3 mL). The resulting mixture was vigorously stirred at 23° C. for 1 h and dried (MgSO4). The drying agent was removed by filtration and the filtrate was concentrated to afford a residue which was dissolved in EtOAc (4 mL). To this solution was added a 1M HCl.Et2O solution dropwise over 1 min. The solid was isolated by concentrated in vacuo to yield 9-methyl-3,4-dihydro-1,5-benzothiazepin-5(2H)-amine hydrochloride (477 mg, 80%) as a brown powder. 1H NMR (CDCl3, 300 MHz): δ7.13 (m, 2H), 6.91 (m, 1H), 4.00-3.80 (br s, 2H), 3.36 (t, 2H, J=5.7 Hz), 2.87 (t, 2H, J=5.7 Hz), 2.42 (s, 3H), 2.05 (m, 2H) ppm.

1. customThe cooling bath was removed once the addition
2. temperaturethe reaction was maintained at 25° C. to 32° C. for 1.5 h
3. additionH2O (0.1 mL) was added cautiously over 5 min
4. dry with materialdried (MgSO4)
5. customThe drying agent was removed by filtration
6. concentrationthe filtrate was concentrated
7. customto afford a residue which
8. customThe solid was isolated
9. concentrationby concentrated in vacuo

ORD record

ord-d9ac586a77064c24a1b185bd25a302bb

Source dataset

uspto-grants-2004_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06713471B1