Acetone → 3,4-bis(p-toluyloxy)phenyl N-(tert-butyl)aminomethyl ketone hydrochloride

HRID 65521Notes

Reaction equation

HRID 65521 reaction equation
[CH3:1][C:2]([CH3:4])=O.[ClH:5].[C:6]([NH:10][CH2:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([OH:21])[CH:15]=1)=[O:13])([CH3:9])([CH3:8])[CH3:7]>C(#N)C>[ClH:5].[C:6]([NH:10][CH2:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([O:20][C:2]2[CH:4]=[CH:8][C:6]([CH3:9])=[CH:7][CH:1]=2)=[C:16]([O:21][C:17]2[CH:18]=[CH:19][C:14]([CH3:12])=[CH:15][CH:16]=2)[CH:15]=1)=[O:13])([CH3:9])([CH3:7])[CH3:8]

Participants

4

Reactant 2

HCID 180AcetoneHCID 30157041-(3,4-Dihydroxyphenyl)-2-((1,1-dimethylethyl)amino)ethan-1-one hydrochloride

Product 1

HCID 704677333,4-bis(p-toluyloxy)phenyl N-(tert-butyl)aminomethyl ketone hydrochlorideYield 64%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The process of Example 1 was repeated substituting acetone for the acetonitrile as solvent. Starting with 26 g of 3,4-dihydroxyphenyl N-(tert-butyl)aminomethyl ketone hydrochloride there was obtained 33 g of 3,4-bis-(p-toluyloxy)phenyl N-(tert-butyl)aminomethyl ketone hydrochloride (64% yield) containing only a trace of tributylamine hydrochloride.

Sources & evidence

ORD record
ord-d46a8f2707ab496ebc72f32a0fd139ff
Source dataset
uspto-grants-1986_09
Patent number
US04614830

Reaction notes

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