Tetrahydrofuran → HCID 21278841, compound

A mixture of 5-chloro-3-[(4-methyleneamino-1-piperazinyl)carbonylmethyl]-2-benzothiazolinone (5.09 g), sodium borohydride (284 mg), tetrahydrofuran (80 ml), and ethanol (70 ml) was stirred for 3 hours at room temperature. The reaction mixture was concentrated under reduced pressure and the residue obtained was purified by column chromatography on silica gel eluting with a mixture of chloroform and methanol (20:1). The fractions containing the desired compoundwere combined and concentrated under reduced pressure. The white residue was dissolved in chloroform (5 ml), and 20% solution of hydrogen chloride in ethanol (1 ml) was added to the above solution. The white precipitates were filtered and recrystallized from a mixture of ethanol (10 ml) and water (2 ml) to give colorless crystals of 5-chloro-3-[(4-methylamino-1-piperazinyl)carbonylmethyl]-2-benzothiazolinone hydrochloride (0.5 g).

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. customthe residue obtained
3. customwas purified by column chromatography on silica gel eluting with a mixture of chloroform and methanol (20:1)
4. additionThe fractions containing the
5. concentrationconcentrated under reduced pressure
6. dissolutionThe white residue was dissolved in chloroform (5 ml)
7. addition20% solution of hydrogen chloride in ethanol (1 ml) was added to the above solution
8. customThe white precipitates
9. filtrationwere filtered
10. customrecrystallized from a mixture of ethanol (10 ml) and water (2 ml)

ORD record

ord-fda073286922476b888dfc1f5367835b

Source dataset

uspto-grants-1989_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04797399