Triethylamine → 2-(N-[4-(1,1-Dioxido-3-oxo-2,3-dihydro-benzisothiazol-2-yl)butyl]aminomethyl)chroman

https://huagongshe.com/reaction/1720344

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	1,1-Dioxido-2-(4-bromobutyl)-1,2-benzisothiazol-3(2H)-one	HCID 10781774	—
Reactant	1-(3,4-dihydro-2H-1-benzopyran-2-yl)methanamine	HCID 11263686	—
Solvent	Dimethylformamide	HCID 6228	—
Product	2-(N-[4-(1,1-Dioxido-3-oxo-2,3-dihydro-benzisothiazol-2-yl)butyl]aminomethyl)chroman	HCID 9822317	—

Reaction Conditions

Temperature	60 °C

Reaction Steps

The mixture of 5.4 g (0.033 mol) (-)-2-aminomethylchroman (example 92f; αD =-122.8), 6.1 g (0.06 mol) triethylamine, 9.5 g (0.03 mol) N-(4-bromobutyl) saccharin and 80 ml anhydrous dimethyl formamide was heated to 60° C. for 4 h. The solvent was evaporated at 0.01 torr. The residue (13.5 g) was dissolved in toluene/ethyl acetate (5:1) and chromatographed on silica (300 g). The fraction (5.8 g) obtained by elution with toluene/ethyl acetate 1:1 was rechromatographed on 150 g of silica, providing 3.7 g of chemically pure 2-(N-[4-(1,1-Dioxido-3-oxo-2,3-dihydro-benzisothiazol-2-yl)butyl]aminomethyl)chroman.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US05506246
Source dataset	uspto-grants-1996_04
ORD ID	ord-dfa01cbd1c9b467aa166ca500d7f4c87
Source note	uspto-grants-1996_04