Ethanol → HCID 86674088, compound

HRID 337222Notes

Reaction equation

[C:1]([O:5][C:6](=[O:27])[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[C:19]([Cl:26])[CH:18]=2)(=[O:16])=[O:15])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C(O)C.[Cl-].[NH4+]>[Fe].O>[C:1]([O:5][C:6](=[O:27])[NH:7][CH:8]1[CH2:9][CH2:10][N:11]([S:14]([C:17]2[CH:22]=[CH:21][C:20]([NH2:23])=[C:19]([Cl:26])[CH:18]=2)(=[O:16])=[O:15])[CH2:12][CH2:13]1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 80 °C

Procedure

[1-(3-Chloro-4-nitro-benzenesulfonyl)-piperidin-4-yl]-carbamic acid tert-butyl ester (0.44 g, 1.05 mmol) was suspended in a 5:1 mixture of ethanol and water (30 ml). To this solution was added iron powder (0.29 g, 5.24 mmol) followed by saturated ammonium chloride solution (3 ml) and the mixture was heated to 80° C. for three hours. After this time, the reaction mixture was cooled to room temperature and filtered through a pad of celite, the celite was washed with ethanol (10 ml) and EtOAc (50 ml) and the solution was concentrated under vacuum. The resulting residue was suspended in water (10 ml) and the solid precipitate collected by filtration and dried under vacuum to give the title compound (0.11 g, 18% yield) as a white solid. Tr=2.12 min, m/z (ES+) (M+Na)+ 412.

Workup

temperatureAfter this time, the reaction mixture was cooled to room temperature
filtrationfiltered through a pad of celite
washthe celite was washed with ethanol (10 ml) and EtOAc (50 ml)
concentrationthe solution was concentrated under vacuum
filtrationthe solid precipitate collected by filtration
customdried under vacuum

Sources & evidence

ORD record: ord-dffb06ed7a8444a2a6cdb7fe8eb09efb
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889716B2

Reaction notes

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