N-(1,1-Dimethylethyl)-1,3-propanediamine → N-[3-[(1,1-Dimethylethyl)amino]propyl]-4,5-diphenyl-1H-imidazole-1-acetamide

HRID 1088295Notes

Reaction equation

[C:1]1([C:7]2[N:8]=[CH:9][N:10]([CH2:18][C:19]([O:21]CC)=O)[C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:24]([NH:28][CH2:29][CH2:30][CH2:31][NH2:32])([CH3:27])([CH3:26])[CH3:25].[H-].[H-].[H-].[H-].[Li+].[Al+3].C(NCCC#N)(C)(C)C>C1COCC1.C(Cl)Cl.O>[CH3:25][C:24]([NH:28][CH2:29][CH2:30][CH2:31][NH:32][C:19](=[O:21])[CH2:18][N:10]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]=[CH:9]1)([CH3:27])[CH3:26]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 7.0 g (23 mmol) of ethyl 4,5-diphenyl-1H-imidazole-1-acetate of example 1 and 4.5 g (34.6 mmol) of 3-(t-butylamino)propylamine, conveniently made by LAH reduction of 3-(t-butylamino)propionitrile in THF, was heated at 100° C. for 8 hr. The residue was distributed between water and methylene chloride, and the methylene chloride layer was dried over MgSO4 and stripped. The residue was recrystallized from ether and then cyclohexane to yield 4.5 g of product, mp 94°-96° C.

Workup

dry with materialthe methylene chloride layer was dried over MgSO4
customThe residue was recrystallized from ether

Sources & evidence

ORD record: ord-c994c8e965704442a0afefbd84abbe5a
Source dataset: uspto-grants-1990_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04962120

Reaction notes

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