Ethyl Acetate → Ethyl 1-(4-cyanonaphthalen-1-yl)piperidine-3-carboxylate

HRID 916359Notes

Reaction equation

[C:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6](F)=[CH:5][CH:4]=1)#[N:2].[NH:14]1[CH2:24][CH2:23][CH2:22][CH:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:15]1.C(OCC)(=O)C>N1C=CC=CC=1>[CH2:20]([O:19][C:17]([CH:16]1[CH2:22][CH2:23][CH2:24][N:14]([C:6]2[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)[CH2:15]1)=[O:18])[CH3:21]

Participants

Conditions

Temperature: 115 °C

Procedure

1-Cyano-4-fluoronaphthalene(1.0 g, 5.84 mmol) and ethyl nipecotate (3.63 mL, 23.4 mmol) were dissolved in pyridine (5 mL) and stirred at 115° C. for 20 hours. After cooling to rt ethyl acetate (50 mL) was added and the solution washed with HCl (0.4 M, 2×30 mL). The combined aqueous layers were extracted with ethyl acetate (30 mL). The combined organic layers were washed with sat. sodium hydrogen carbonate (30 mL), brine (30 mL), dried and evaporated. The crude product was purified by silica gel column chromatography eluted with a stepwise gradient of 0-70% ethyl acetate in n-heptane to give the title compound (1.23 g, 68%) as a yellowish oil

Workup

additionwas added
washthe solution washed with HCl (0.4 M, 2×30 mL)
extractionThe combined aqueous layers were extracted with ethyl acetate (30 mL)
washThe combined organic layers were washed with sat. sodium hydrogen carbonate (30 mL), brine (30 mL)
customdried
customevaporated
customThe crude product was purified by silica gel column chromatography
washeluted with a stepwise gradient of 0-70% ethyl acetate in n-heptane

Sources & evidence

ORD record: ord-c4705b46d65a4adb9140393da9f62649
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07268232B2

Reaction notes

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