Piperidine → HCID 66761100, compound

HRID 2063826Notes

Reaction equation

[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].CC(N(C)C)=O.[Br:19][C:20]1[C:21]([CH3:34])=[C:22]([CH3:33])[C:23]2[O:27][C:26]([CH2:29]I)([CH3:28])[CH2:25][C:24]=2[C:31]=1[CH3:32]>C(OCC)(=O)C.O>[Br:19][C:20]1[C:21]([CH3:34])=[C:22]([CH3:33])[C:23]2[O:27][C:26]([CH2:28][N:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)([CH3:29])[CH2:25][C:24]=2[C:31]=1[CH3:32]

Participants

Conditions

Temperature: 150 °C

Procedure

Piperidine (323 mg, 3.80 mmol) and potassium carbonate (525 mg, 3.80 mmol) were added to a solution of DMA (3 mL) containing 5-bromo-2-(iodomethyl)-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran (300 mg, 0.759 mmol) synthesized in Reference Example 133, and the mixture was stirred under microwave irradiation at 150° C. for 10 minutes. The reaction solution was cooled to room temperature, and water and ethyl acetate were added thereto to separate an organic layer. The organic layer was washed with water and saturated saline, and dried using anhydrous magnesium sulfate, followed by concentration under reduced pressure. The residue was purified by silica gel chromatography (hexane-ethyl acetate 95:5-85:15) to give 170 mg of the title compound (yield: 64%).

Workup

customsynthesized in Reference Example 133
temperatureThe reaction solution was cooled to room temperature
customto separate an organic layer
washThe organic layer was washed with water and saturated saline
customdried
concentrationfollowed by concentration under reduced pressure
customThe residue was purified by silica gel chromatography (hexane-ethyl acetate 95:5-85:15)

Sources & evidence

ORD record: ord-64ea433322af429cbc39d4ee5d15bb17
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288390B2

Reaction notes

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