Diisopropylethylamine → 1-Benzyl-4-methylpiperidin-3-one

HRID 2122042Notes

Reaction equation

C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:12]([N:19]1[CH2:24][CH2:23][CH:22]([CH3:25])[CH:21]([OH:26])[CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(C(C)C)CC)(C)C>ClCCl.CS(C)=O>[CH2:12]([N:19]1[CH2:24][CH2:23][CH:22]([CH3:25])[C:21](=[O:26])[CH2:20]1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of the product from Method D (9.8 grams/0.026 mol) and 31.7 mL of diisopropylethylamine dissolved in 250 mL of dichloromethane and cooled to 0° C. was added (dropwise) 12.4 grams of SO3 pyridine complex dissolved in 153 mL of dimethylsulfoxide over a 40 minute period. Once added, the reaction stirred for 1.5 hours at room temperature and was then quenched upon addition of 200 mL of saturated NaHCO3 (aq). The dichloromethane was removed in vacuo and the remaining aqueous residue extracted four times with diisopropyl ether (150 mL). The combined ether layers were washed four times with water (100 mL), dried over Na2SO4 and concentrated to dryness in vacuo affording 3.81 grams (72.97%) of the title compound as yellow oil. LRMS: 204 (M+1).

Workup

additionwas added (dropwise) 12.4 grams of SO3 pyridine complex
additionOnce added
customwas then quenched upon addition of 200 mL of saturated NaHCO3 (aq)
customThe dichloromethane was removed in vacuo
extractionthe remaining aqueous residue extracted four times with diisopropyl ether (150 mL)
washThe combined ether layers were washed four times with water (100 mL)
dry with materialdried over Na2SO4
concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record: ord-c6b46e52a69b422e9fe0e2136f9fc50f
Source dataset: uspto-grants-2004_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06696567B2

Reaction notes

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