Methyl iodide → Ethyl 4-methyl-3-oxo-1-(phenylmethyl)-4-piperidinecarboxylate

HRID 1867375Notes

Reaction equation

[CH3:1]C([O-])(C)C.[K+].Cl.[CH2:8]([O:10][C:11]([CH:13]1[CH2:18][CH2:17][N:16]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:15][C:14]1=[O:26])=[O:12])[CH3:9].IC.[NH4+].[Cl-]>C1COCC1>[CH2:8]([O:10][C:11]([C:13]1([CH3:1])[CH2:18][CH2:17][N:16]([CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:15][C:14]1=[O:26])=[O:12])[CH3:9]

Participants

Conditions

Temperature: 0 °C

Procedure

A milky solution of 7.75 g (69.02 mmol) of potassium tert-butylate in 125 ml of THF was cooled (0° C.) and treated portion wise with 10.44 g (34.00 mmol) of ethyl-N-benzyl-3-oxo-4-piperidin-carboxylate hydrochloride so the temperature did not rise over 5° C. After 1 h at RT, the reaction was cooled (0° C.) and ad treated slowly with 5.07 ml (35.70 mmol) of iodomethane in 4 ml of THF. After 4.5 h at RT, the reaction was cooled (0° C.) and neutralized with 40 ml of aqueous saturated NH4Cl solution. The aqueous phase was extracted with Et2O (3×). The organic phases were washed with aqueous saturated NaCl, dried over Na2SO4 and evaporated to give 4.97 g (53%) of the title compound as orange oil. MS: 276.1 (MH+).

Workup

customdid not rise over 5° C
waitAfter 4.5 h at RT
temperaturethe reaction was cooled (0° C.)
extractionThe aqueous phase was extracted with Et2O (3×)
washThe organic phases were washed with aqueous saturated NaCl
dry with materialdried over Na2SO4
customevaporated

Sources & evidence

ORD record: ord-405ae6eeff3644dcaf2623c66f161b6a
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07632829B2

Reaction notes

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