Dodecanoyl chloride → N-(2,6-Diphenyl-3,5-dimethylpiperidin-4-yl)lauramide

HRID 1646784Notes

Reaction equation

[C:1]1([CH:7]2[CH:12]([CH3:13])[CH:11]([NH2:14])[CH:10]([CH3:15])[CH:9]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:29](Cl)(=[O:41])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40]>C(Cl)Cl>[C:16]1([CH:9]2[CH:10]([CH3:15])[CH:11]([NH:14][C:29](=[O:41])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH:12]([CH3:13])[CH:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[NH:8]2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred 0° C. solution of 12.7 g (45.3 mmol) of 2,6-diphenyl-3,5-dimethyl-4-aminopiperidine and 5.1 g (50 mmol) of triethylamine in 150 ml of methylene chloride is added dropwise a solution of 9.9 g (45.3 mmol) of lauroyl chloride. After stirring for 30 minutes at 0° C., the reaction mixture is washed with water (2×200 ml) followed by a saturated aqueous sodium bicarbonate solution (300 ml). The organic phase is separated, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting solid is recrystallized from ethanol to give 15.4 g (73% yield) of the title compound as a white solid melting at 112°-114° C.

Workup

washthe reaction mixture is washed with water (2×200 ml)
customThe organic phase is separated
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe resulting solid is recrystallized from ethanol

Sources & evidence

ORD record: ord-02e78b583864428fb63df55a9ec25e2b
Source dataset: uspto-grants-1993_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05180829

Reaction notes

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