1-Methyl-1H-imidazol-2-amine → 1-(1-methyl-1H-imidazole-2-yl)-4-(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)piperazine

HRID 1850505Notes

Reaction equation

HRID 1850505 reaction equation
Cl[CH2:2][CH2:3][N:4]([CH2:19][CH2:20]Cl)[C:5]1[C:6]([CH3:18])=[C:7]([CH3:17])[C:8]2[O:12][C:11]([CH3:14])([CH3:13])[CH2:10][C:9]=2[C:15]=1[CH3:16].[CH3:22][N:23]1[CH:27]=[CH:26][N:25]=[C:24]1[NH2:28]>>[CH3:22][N:23]1[CH:27]=[CH:26][N:25]=[C:24]1[N:28]1[CH2:20][CH2:19][N:4]([C:5]2[C:6]([CH3:18])=[C:7]([CH3:17])[C:8]3[O:12][C:11]([CH3:14])([CH3:13])[CH2:10][C:9]=3[C:15]=2[CH3:16])[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 5663211-Methyl-1H-imidazol-2-amineHCID 66760837N,N-bis(2-chloroethyl)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-amine

Product 1

HCID 594850741-(1-methyl-1H-imidazole-2-yl)-4-(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)piperazineYield 51.9%

Procedure

By using N,N-bis(2-chloroethyl)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-amine (330 mg, 1.0 mmol) synthesized in Reference Example 146 and 1-methyl-1H-imidazole-2-amine (146 mg, 1.5 mmol), the reaction was carried out in the same manner as Example 117 to obtain 184 mg of the title compound as an oily product (yield 52%).

Sources & evidence

ORD record
ord-165922782e7448b5aad03781db869b3f
Source dataset
uspto-grants-2015_02
Patent number
US08957069B2

Reaction notes

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