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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 635414Generated: November 3, 2026

Dimethylformamide → (+/-)-N-[3-[2-[2-(dibenzofuran-3-yloxy)ethylamino]-1-hydroxyethyl]phenyl]methanesulfonamide Hydrochloride

https://huagongshe.com/reaction/635414

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
ReactantN-[3-(2-bromoacetyl)phenyl]methanesulfonamideHCID 11346858—
Reactant2-(Dibenzo[b,d]furan-3-yloxy)ethanamineHCID 18615231—
ReactantEthanol hydrochlorideHCID 21887872—
SolventChloroform methanolHCID 21584188—
Product(+/-)-N-[3-[2-[2-(dibenzofuran-3-yloxy)ethylamino]-1-hydroxyethyl]phenyl]methanesulfonamide HydrochlorideHCID 18615217—

Reaction Steps

Following the procedures of Example 7, the above-identified compound was synthesized from 224.6 mg of Intermediate 5 and 170 mg of Intermediate 14, with the proviso that the following modification was incorporated. Thus, addition of dimethylformamide was omitted and the purification of the crude product was effected twice by a chromatography (methanol/chloroform of 1/20-1/10). The free amine compound (98.4 mg) was converted into its hydrochloride salt (the above-identified compound) with 1.1 eq. of 0.1 N hydrogenchloride/ethanol, whereupon the solvent was evaporated off under a reduced pressure. To the resulting residue was added diethyl ether and the deposited precipitate was washed diethyl ether and dried under a reduced pressure at 46° C., whereby the above-identified compound was obtained as a powdery product. Rf=0.27 (methanol/chloroform of 1/10).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06187809B1
Source datasetuspto-grants-2001_02
ORD IDord-4b1a35ad2cff4e5f8b5c8acc8ce73ad9
Source noteuspto-grants-2001_02