4-Iodotoluene → 1-(4-Methylphenyl)-4-(2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran-5-yl)piperazine

HRID 2063844Notes

Reaction equation

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

Participants

Reactant 2

HCID 122074-Iodotoluene

HCID 667598101-(2,4,6,7-Tetramethyl-2,3-dihydro-1-benzofuran-5-yl)piperazine

Product 1

HCID 594850021-(4-Methylphenyl)-4-(2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran-5-yl)piperazineYield 33%

Procedure

By using 1-(2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran-5-yl)piperazine (700 mg, 2.69 mmol) synthesized in Reference example 56 and 4-iodotoluene (1.76 g, 8.08 mmol), the reaction was carried out in the same manner as Example 23 to synthesize the title compound 310 mg (yield 33%). Melting point was 150 to 151° C. (ethanol).

Sources & evidence

ORD record: ord-a4c4c197b1b94f368e8f8411b28cc2b5
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288390B2

Reaction notes

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