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

HRID 1646780Notes

Reaction equation

HRID 1646780 reaction equation
[C:1]1([CH:7]2[CH:12]([CH3:13])[CH:11]([OH:14])[CH2:10][CH:9]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])CCC.[C:26](Cl)(=[O:38])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]>>[C:26]([O:14][CH:11]1[CH2:10][CH:9]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[NH:8][CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:12]1[CH3:13])(=[O:38])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]

Participants

4

Reactant 3

HCID 8166Dodecanoyl chlorideHCID 27298003-Methyl-2,6-diphenyl-4-piperidinolHCID 178418339Butyllithium

Product 1

HCID 540525282,6-Diphenyl-3-methylpiperidin-4-yl LaurateYield 65.3%

Procedure

The general procedure of Example 1 is repeated using 22.8 g (85.2 mmol) of 2,6-diphenyl-3-methyl-4-hydroxypiperidine, 34 mL (85 mmol) of n-butyllithium (2.5M in hexanes) and 18.6 g (85.2 mmol) of lauroyl chloride. 25.0 g (65% yield) of the title compound is isolated after purification by LC (silica gel, ethyl acetate/hexane): mp 56°-59° C.

Sources & evidence

ORD record
ord-50844e71cfce4de7816967d16c032627
Source dataset
uspto-grants-1993_01
Patent number
US05180829

Reaction notes

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