N-3-Bromopropylphthalimide → 2-(3-(4-methyl-1H-imidazol-1-yl)propyl)isoindoline-1,3-dione

HRID 1154331Notes

Reaction equation

HRID 1154331 reaction equation
Br[CH2:2][CH2:3][CH2:4][N:5]1[C:9](=[O:10])[C:8]2=[CH:11][CH:12]=[CH:13][CH:14]=[C:7]2[C:6]1=[O:15].[CH3:16][C:17]1[N:18]=[CH:19][NH:20][CH:21]=1.[CH2:22]([C:24]1[NH:25][CH:26]=[CH:27][N:28]=1)[CH3:23]>>[CH3:16][C:17]1[N:18]=[CH:19][N:20]([CH2:2][CH2:3][CH2:4][N:5]2[C:9](=[O:10])[C:8]3[C:7](=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:6]2=[O:15])[CH:21]=1.[CH2:22]([C:24]1[N:25]([CH2:2][CH2:3][CH2:4][N:5]2[C:9](=[O:10])[C:8]3[C:7](=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:6]2=[O:15])[CH:26]=[CH:27][N:28]=1)[CH3:23]

Participants

5

Reactant 3

HCID 21611N-3-BromopropylphthalimideHCID 661302-EthylimidazoleHCID 178418800HCID 178418800, compound

Product 2

HCID 136181202-(3-(4-methyl-1H-imidazol-1-yl)propyl)isoindoline-1,3-dioneHCID 136181212-[3-(2-ethyl-1H-imidazol-1-yl)-propyl]isoindole-1,3(2H)-dione

Procedure

Following the procedure of this example, N-(3-bromopropyl)phthalimide with 4-methylimidazole and 2-ethylimidazole were used to produce respectively 2-[3-(4-methyl-1H-imidazol-1-yl)propyl]isoindole-1,3-(2H)-dione and 2-[3-(2-ethyl-1H-imidazol-1-yl)-propyl]isoindole-1,3(2H)-dione which again following the procedure of this example were converted respectively to (4-methyl-1H-imidazol-1-yl)-1-propanamine dihydrochloride and (2-ethyl-1H-imidazol-1-yl)-1-propanamine dihydrochloride which were then converted by the procedure of Example 1, using the appropriate acid chloride, to the products of Examples 21-27, listed in Table V.

Sources & evidence

ORD record
ord-0a6365ca304746efbdac8c271989a1d4
Source dataset
uspto-grants-1984_12
Patent number
US04489089

Reaction notes

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