Potassium Carbonate → HCID 13298561, compound

HRID 2417616Notes

Reaction equation

CS(O)(=O)=O.[N:6]1([C:12]2[C:13](=[O:19])[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:27][C:28]([C:30]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[C:32]([O:38][CH3:39])[CH:31]=1)=[O:29]>C(#N)C>[CH3:39][O:38][C:32]1[CH:31]=[C:30]([C:28](=[O:29])[CH2:27][N:9]2[CH2:8][CH2:7][N:6]([C:12]3[C:13](=[O:19])[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:11][CH2:10]2)[CH:35]=[CH:34][C:33]=1[O:36][CH3:37]

Participants

Conditions

Temperature: 85 °C

Procedure

To a suspension of 2-(1-piperazinyl)-2,4,6-cycloheptatrien-1-one methane sulfonate (19.64 g, described in Example 2) in acetonitrile, (150 ml) was added potassium carbonate (20.8 g). The resulting suspension was refluxed for about 20 min. A solution of 2-bromo-1-(3,4-dimethoxyphenyl)-1-ethanone (17.8 g) in acetonitrile (100 ml) was added dropwise. The mixture was stirred at 85° C. for 1.25 hr. The mixture was filtered and the filtrate was evaporated. The filtered solid and oily residue was taken up in chloroform-water, and the chloroform layer was dried and evaporated to yield crude product (24.17 g). Chromatographic purification on silica gel (1000 gel) using ethyl acetate gave 2-[4-[2-(3,4-dimethoxyphenyl)-2-oxoethyl]-1-piperazinyl]-2,4,6-cycloheptatrien-1-one (8.2 g), mp 132°-135° C.

Workup

temperatureThe resulting suspension was refluxed for about 20 min
filtrationThe mixture was filtered
customthe filtrate was evaporated
dry with materialthe chloroform layer was dried
customevaporated
customto yield crude product (24.17 g)
customChromatographic purification on silica gel (1000 gel)

Sources & evidence

ORD record: ord-113db1c5475a49919abf2283000edb06
Source dataset: uspto-grants-1984_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04469695

Reaction notes

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