Piperidine → HCID 59232953, compound

HRID 2426982Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:9]([CH3:15])([CH3:14])[C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.[NH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:14][C:9]([CH3:15])([CH:8]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:5]1[CH:6]=[CH:7][C:2]([N:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[CH:3][CH:4]=1)[C:10]([O:12][CH3:13])=[O:11]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of methyl 3-(4-bromophenyl)-2,2-dimethyl-3-phenylpropanoate (250 mg, 0.72 mmol), piperidine (3 mL), palladium acetate (32 mg, 0.144 mmol), 2-(di-tert-butylphosphino)-biphenyl (87 mg, 0.29 mmol), and sodium tert-butoxide (166 mg, 1.73 mmol) in toluene (5 ml) was heated at 80° C. for 1.5 h. The reaction mixture was cooled to room temperature, the solid was removed by filtration, and the filtrate was concentrated in vacuo. The crude product was purified by silica gel flash chromatography using 10% ethyl acetate in hexanes to give methyl 2,2-dimethyl-3-phenyl-3-(4-(piperidin-1-yl)phenyl)propanoate as a white solid (207 mg, 82%). LC/MS (m/z) 352.24 [(M+H)+]; HPLC Rt: 2.448 min.

Workup

temperatureThe reaction mixture was cooled to room temperature
customthe solid was removed by filtration
concentrationthe filtrate was concentrated in vacuo
customThe crude product was purified by silica gel flash chromatography

Sources & evidence

ORD record: ord-5a42047e86654a9e8bd5c0c3c0a9b040
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07968577B2

Reaction notes

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