Hydrochloric Acid → cis-N-[2-(4-bromophenoxy)cyclopentyl]propane-2-sulfonamide

HRID 2360331Notes

Reaction equation

[Br:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][C@H:7]2[CH2:11][CH2:10][CH2:9][C@H:8]2[NH2:12])=[CH:4][CH:3]=1.N12CCCN=C1CCCCC2.[CH3:26][CH:27]([S:29](Cl)(=[O:31])=[O:30])[CH3:28].Cl>C(Cl)Cl.CN(C)C1C=CN=CC=1>[Br:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][C@H:7]2[CH2:11][CH2:10][CH2:9][C@H:8]2[NH:12][S:29]([CH:27]([CH3:28])[CH3:26])(=[O:31])=[O:30])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a slurry of cis-2-(4-bromophenoxy)cyclopentanamine (1.43 g, 5.58 mmol) in methylene chloride (38.5 mL) was added 1,8-diazabicyclo[5.4.0]undec-7-ene (1.40 mL, 9.36 mmol), then 4-(dimethylamino)pyridine (915 mg, 7.49 mmol). The reaction mixture was cooled to 0° C. and propane-2-sulfonyl chloride (0.937 mL, 8.38 mmol) was added drop-wise. The mixture was then allowed to warm to room temperature and stir for 18 hours. The reaction was treated with 1N aqueous hydrochloric acid, and the organic layer was washed with saturated aqueous sodium chloride solution, dried over calcium sulfate, filtered and concentrated in vacuo. The resulting residue was purified by silica gel chromatography (Gradient: 0% to 15% ethyl acetate in heptane) to provide product as a colorless gum. Yield: 1.586 g, 4.38 mmol, 78%.

Workup

temperatureto warm to room temperature
washthe organic layer was washed with saturated aqueous sodium chloride solution
dry with materialdried over calcium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe resulting residue was purified by silica gel chromatography (Gradient: 0% to 15% ethyl acetate in heptane)
customto provide product as a colorless gum

Sources & evidence

ORD record: ord-ea0c8450fb644cb693ed3cf77d7bc8e3
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08686043B2

Reaction notes

Loading…