Potassium Carbonate → HCID 22111037, compound

HRID 565676Notes

Reaction equation

Br[CH2:2][C:3]1([CH3:15])[CH2:7][C:6]2[C:8]([CH3:14])=[CH:9][C:10]([CH3:13])=[C:11]([CH3:12])[C:5]=2[O:4]1.[C:16]1([CH:22]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[NH:23][CH:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C(=O)C.O>[CH3:15][C:3]1([CH2:2][N:27]2[CH2:28][CH2:29][CH:24]([NH:23][CH:22]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:25][CH2:26]2)[CH2:7][C:6]2[C:8]([CH3:14])=[CH:9][C:10]([CH3:13])=[C:11]([CH3:12])[C:5]=2[O:4]1

Participants

Conditions

Temperature: 177 °C

Procedure

A suspension of 2-bromomethyl-2,3-dihydro-2,4,6,7-tetramethylbenzofuran (1.0 g), N-(diphenylmethyl)-4-piperidinamine (1.5 g), and potassium carbonate (0.77 g) in N,N-dimethylacetamide (4 mL) was stirred under argon gas at 177° C. for 4 hours. This reaction mixture was diluted with water and extracted with ethyl acetate. The extract was washed with water and saturated aqueous sodium chloride solution, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=7:3) to provide the title compound (1.5 g). Yield 97%.

Workup

extractionextracted with ethyl acetate
washThe extract was washed with water and saturated aqueous sodium chloride solution
dry with materialdried over MgSO4
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=7:3)

Sources & evidence

ORD record: ord-a89309e7fed14249b80b909772733834
Source dataset: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06172085B2

Reaction notes

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