Dodecanoyl chloride → 2,6-Diphenyl-3,5-dimethylpiperidin-4-yl Laurate

HRID 257679Notes

Reaction equation

[C:1]1([CH:7]2[CH:12]([CH3:13])[CH:11]([OH: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([Li])CCC.[C:27](Cl)(=[O:39])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]>>[C:27]([O:14][CH:11]1[CH:12]([CH3:13])[CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[NH:8][CH:9]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:10]1[CH3:15])(=[O:39])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]

Participants

Reactant 3

HCID 8166Dodecanoyl chloride

HCID 3382063,5-Dimethyl-2,6-diphenylpiperidin-4-ol

HCID 178418339Butyllithium

Product 1

HCID 536852752,6-Diphenyl-3,5-dimethylpiperidin-4-yl LaurateYield 74.4%

Procedure

The general procedure of Example 1 is repeated using 28.1 g (0.10 mol) of 2,6-diphenyl-3,5-dimethyl-4-hydroxypiperidine, 40 mL (0.10 mol) of n-butyllithium (2.5M in hexanes) and 21.8 g (0.10 mol) of lauroyl chloride. 34.5 g (74% yield) of the title compound is isolated after purification by LC (silica gel, ethyl acetate/hexane): mp 74°-76° C.

Sources & evidence

ORD record: ord-483069f8e59d42c785cb680c18c89d97
Source dataset: uspto-grants-1993_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05262538

Reaction notes

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