Decanoyl chloride → Decanoic acid 1,1-diethyl-3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propyl ester hydrochloride

To a solution of 6-fluoro-3-[1-(3-hydroxy-3-ethylpentyl)-4-piperidinyl]-1,2-benzisoxazole (2.5 g, 7.48 mmol) in DCM (100 ml) was added decanoyl chloride (1.5 ml, 7.48 mmol) at 0° C., under nitrogen. The reaction mixture was stirred for 4 days at which time it was poured into NaHCO3 (sat., 50 ml). The layers were separated and the aqueous phase was extracted with DCM (2X). The combined organics were dried, filtered and concentrated to give the crude product which was purified via flash column chromatography (silica gel, 20-40% EtOAc/DCM). The product containing fractions were concentrated to give 3.0 g (81%) of the desired product as a yellow oil. The hydrochloride salt was prepared in anhydrous ether (60 ml) and isopropanol (1 ml) with ethereal HCl. The white salt was filtered and washed with anhydrous ether, m.p.=159°-161° C.

1. customThe layers were separated
2. extractionthe aqueous phase was extracted with DCM (2X)
3. customThe combined organics were dried
4. filtrationfiltered
5. concentrationconcentrated
6. customto give the crude product which
7. customwas purified via flash column chromatography (silica gel, 20-40% EtOAc/DCM)
8. additionThe product containing fractions
9. concentrationwere concentrated

ORD 기록

ord-929bc3aeabda4da8a0926967ea4bbaf0

출처 데이터셋

uspto-grants-1997_01

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US05591745