Sodium Iodide → HCID 68851665, compound

HRID 490958Notes

Reaction equation

[C:1]1([S:7]([C:10]2[CH:19]=[C:18]3[C:13]([CH:14](Cl)[CH2:15][CH2:16][O:17]3)=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:21]([N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1)([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22].[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:24]([O:23][C:21]([N:28]1[CH2:33][CH2:32][N:31]([CH:14]2[C:13]3[C:18](=[CH:19][C:10]([S:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)(=[O:9])=[O:8])=[CH:11][CH:12]=3)[O:17][CH2:16][CH2:15]2)[CH2:30][CH2:29]1)=[O:22])([CH3:27])([CH3:25])[CH3:26]

Participants

Conditions

Temperature: 70 °C

Procedure

7-Benzenesulfonyl-4-chloro-chroman (512 mg, 1.65 mmol), Boc-piperazine (piperazine-1-carboxylic acid tert-butyl ester, 371 mg, 1.92 mmol), sodium iodide (50 mg) and potassium carbonate (275 mg) were added to 5 mL of DMF, and the reaction mixture was heated to 70° C. overnight. The reaction mixture was cooled and partitioned between ethyl acetate and water, and the combined organic layers were dried over MgSO4. Solvent was removed under reduced pressure, and the residue was chromatographed (silica gel, using 30% ethyl acetate in hexanes) to yield 400 mg of 4-(7-Benzenesulfonyl-chroman-4-yl)-piperazine-1-carboxylic acid tert-butyl ester.

Workup

temperatureThe reaction mixture was cooled
custompartitioned between ethyl acetate and water
dry with materialthe combined organic layers were dried over MgSO4
customSolvent was removed under reduced pressure
customthe residue was chromatographed (silica gel, using 30% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-1ebbd3f0f36847a891e572d85a948a27
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07528250B2

Reaction notes

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