Cinnamoylbenzene → (2RS)-(3RS)-2-dimethylaminomethyl-1,3-diphenyl-3-p-tolylpropan-1-one hydrochloride

HRID 481166Notes

Reaction equation

C1(C=CC(C2C=CC=CC=2)=O)C=CC=CC=1.BrC1C=CC(C)=CC=1.[CH3:25][N+:26]([CH3:28])=[CH2:27].[I-].[ClH:30].CN(C)[C:33](C)([CH:42]([C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)[C:43]1[CH:48]=[CH:47][C:46]([CH3:49])=[CH:45][CH:44]=1)[C:34]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:35]>>[ClH:30].[CH3:27][N:26]([CH2:28][CH:33]([CH:42]([C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)[C:43]1[CH:44]=[CH:45][C:46]([CH3:49])=[CH:47][CH:48]=1)[C:34]([C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)=[O:35])[CH3:25]

Participants

Reactant 4

HCID 7189Cinnamoylbenzene

HCID 78054-Bromotoluene

HCID 2724133Dimethyl(methylene)ammounium iodide

HCID 70010556(2RS)-(3RS)-2-dimethylamino-methyl-1,3-diphenyl-3-p-tolylpropan-1-one hydrochloride

Product 1

HCID 18767264(2RS)-(3RS)-2-dimethylaminomethyl-1,3-diphenyl-3-p-tolylpropan-1-one hydrochloride

Procedure

The synthesis was carried out according to the procedure of Example 38 and the chalcone derivative was reacted with 4-bromotoluene. The Eschenmoser salt was then added in an equimolar amount. The yield of (2RS)-(3RS)-2-dimethylamino-methyl-1,3-diphenyl-3-p-tolylpropan-1-one hydrochloride was 0.7 g (41%).

Sources & evidence

ORD record: ord-2f51a961d21b4628bd9082de9c1ccc62
Source dataset: uspto-grants-2003_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06653508B2

Reaction notes

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