Piperidine → 6-(1-Piperidinylsulfonyl)-2H-1,4-benzoxazin-3(4H)-one

HRID 1184436Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:12]([O-])=O.[NH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.C(N(CC)CC)C.Br[CH2:29][C:30](OC)=[O:31]>C(Cl)Cl>[N:15]1([S:8]([C:5]2[CH:6]=[CH:7][C:2]3[O:1][CH2:29][C:30](=[O:31])[NH:12][C:3]=3[CH:4]=2)(=[O:10])=[O:9])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

Conditions

Temperature: 23 °C

Procedure

To a 15 mL screw cap vial was added 4-hydroxy-3-nitrobenzene-1-sulfonyl chloride (238 mg, 1.0 mmol) and piperidine (102 mg, 1.2 mmol) in DCM (5.0 mL) followed by triethylamine (346 μL, 2.5 mmol). After stirring at 23° C. for 1 h, the reaction was concentrated in vacuo and the resulting residue was taken up in sat aqueous NaHCO3. The resulting solid was isolated by filtration, washed with water and dried in vacuo to give a white solid. The material was subsequently alkylated using the general procedure for alkylation of substituted 2-nitrophenols using methyl bromoacetate as the alkylating agent followed by treatment in the general procedure for reduction of nitro group and subsequent ring closure to give the title compound as a white solid: 1H NMR (DMSO-d6, 400 MHz): δ=10.91 (s, 1H), 7.21-7.32 (m, 2H), 7.15 (d, J=8.1 Hz, 1H), 4.71 (s, 2H), 2.85 (t, J=5.1 Hz, 4H), 1.46-1.62 (m, 4H), 1.37 ppm (d, J=5.1 Hz, 2H). ESI-MS: m/z 297.1 (M+H)+.

Workup

customTo a 15 mL screw cap
concentrationthe reaction was concentrated in vacuo
customThe resulting solid was isolated by filtration
washwashed with water
customdried in vacuo
customto give a white solid

Sources & evidence

ORD record: ord-4a34db44df8941b39db9630e869aa410
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08669249B2

Reaction notes

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