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

HRID 1720344Notes

Reaction equation

[NH2:1][CH2:2][CH:3]1[CH2:12][CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[O:4]1.C(N(CC)CC)C.Br[CH2:21][CH2:22][CH2:23][CH2:24][N:25]1[C:35](=[O:36])[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[S:26]1(=[O:28])=[O:27]>CN(C)C=O>[O:27]=[S:26]1(=[O:28])[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:34]=2[C:35](=[O:36])[N:25]1[CH2:24][CH2:23][CH2:22][CH2:21][NH:1][CH2:2][CH:3]1[CH2:12][CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[O:4]1

Participants

Conditions

Temperature: 60 °C

Procedure

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.

Workup

customThe solvent was evaporated at 0.01 torr
dissolutionThe residue (13.5 g) was dissolved in toluene/ethyl acetate (5:1)
customchromatographed on silica (300 g)
customThe fraction (5.8 g) obtained by elution with toluene/ethyl acetate 1:1
customwas rechromatographed on 150 g of silica

Sources & evidence

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

Reaction notes

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