1-(p-Tolyl)piperazine → {2,4,6,7-Tetramethyl-5-[4-(4-methylphenyl)piperazin-1-yl]-2,3-dihydro-1-benzofuran-2-yl}methanol

HRID 2063904Notes

Reaction equation

HRID 2063904 reaction equation
Br[C:2]1[C:3]([CH3:16])=[C:4]([CH3:15])[C:5]2[O:9][C:8]([CH2:11][OH:12])([CH3:10])[CH2:7][C:6]=2[C:13]=1[CH3:14].[CH3:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)=[CH:20][CH:19]=1>>[CH3:10][C:8]1([CH2:11][OH:12])[CH2:7][C:6]2[C:13]([CH3:14])=[C:2]([N:27]3[CH2:28][CH2:29][N:24]([C:21]4[CH:22]=[CH:23][C:18]([CH3:17])=[CH:19][CH:20]=4)[CH2:25][CH2:26]3)[C:3]([CH3:16])=[C:4]([CH3:15])[C:5]=2[O:9]1

Participants

3

Reactant 2

HCID 831131-(p-Tolyl)piperazineHCID 66759014(5-Bromo-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran-2-yl)methanol

Product 1

HCID 59485073{2,4,6,7-Tetramethyl-5-[4-(4-methylphenyl)piperazin-1-yl]-2,3-dihydro-1-benzofuran-2-yl}methanolYield 6.8%

Procedure

By using (5-bromo-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran-2-yl)methanol (360 mg, 1.16 mmol) synthesized in Reference example 123 and 1-(4-methylphenyl)piperazine (668 mg, 3.79 mmol), the reaction was carried out in the same manner as Example 1 to obtain the title compound 30 mg (yield 6%). Melting point was 152 to 155° C. (ethyl acetate-hexane).

Sources & evidence

ORD record
ord-9fa94ef7abed41cf895f6b5ce52c260f
Source dataset
uspto-grants-2012_10
Patent number
US08288390B2

Reaction notes

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