Sodium Carbonate → N-(2-Carbomethoxyphenyl)-4-piperidone

HRID 842790Notes

Reaction equation

C1O[C:5]2([CH2:10][CH2:9][N:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[C:17]([O:19][CH3:20])=[O:18])[CH2:7][CH2:6]2)[O:4]C1C.C(=O)([O-])[O-].[Na+].[Na+]>Cl.O>[C:17]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[N:8]1[CH2:7][CH2:6][C:5](=[O:4])[CH2:10][CH2:9]1)([O:19][CH3:20])=[O:18]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 44 (5.3 g, 18 mmol) in methanolic HCl (200 mL) was heated in an oil bath (50° C., 1 h). The resulting mixture was cooled, diluted with water (50 mL), and stirred at room temperature (30 min). The solvent volume was reduced in vacuo and neutralized with sodium carbonate. The aqueous layer was extracted with three portions of dichloromethane. The combined organic extracts were washed with brine and dried over Na2SO4. The solvent was removed in vacuo. PCTLC (SiO2, 6 mm, 10% EtOH-90% CHCl3) afforded the title compound (45).

Workup

temperatureThe resulting mixture was cooled
extractionThe aqueous layer was extracted with three portions of dichloromethane
washThe combined organic extracts were washed with brine
dry with materialdried over Na2SO4
customThe solvent was removed in vacuo

Sources & evidence

ORD record: ord-5058f90ec1b24f22896270822b1af774
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06376503B1

Reaction notes

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