Dimethyldioxirane → N-(1-Hydroxy-2,6-diphenyl-3,5-dimethylpiperidin-4-yl)lauramide

HRID 257682

Reaction equation

HRID 257682 reaction equation
[C:1]1([CH:7]2[CH:12]([CH3:13])[CH:11]([NH:14][C:15](=[O:27])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH:10]([CH3:28])[CH:9]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC1(C)O[O:37]1>CC(C)=O>[OH:37][N:8]1[CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:12]([CH3:13])[CH:11]([NH:14][C:15](=[O:27])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH:10]([CH3:28])[CH:9]1[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

4

Reactant 2

HCID 115197DimethyldioxiraneHCID 18954068N-(2,6-Diphenyl-3,5-dimethylpiperidin-4-yl)lauramide

Product 1

HCID 18954070N-(1-Hydroxy-2,6-diphenyl-3,5-dimethylpiperidin-4-yl)lauramide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Following the general procedure of Example 2 and using 8.56 g (18.5 mmol) of N-(2,6-diphenyl-3,5-dimethylpiperidin-4-yl)lauramide, prepared in Example 11, and 462 ml of a 0.04 molar solution of dimethyldioxirane (18.5 mmol) in acetone, the title compound is isolated in a yield of 7.37 g (70%) after purification by LC (silica gel; ethyl acetate:hexanes) as a white solid melting at 58°-62° C.

Sources & evidence

ORD record
ord-f164c3033b6f4fd29e3a3ffdd6d970c8
Source dataset
uspto-grants-1993_11
Patent number
US05262538

Linked notes

Loading…