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

HRID 2060836Notes

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-e9f6b404b4da4c7ca468141ba4129922
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08278457B2

Reaction notes

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