p-Xylyl bromide → 1-(4-Methoxyphenyl)-4-(2,2,4,6,7-pentamethyl-3-(4-methylbenzyl)oxy-2,3-dihydro-1-benzofuran-5-yl)piperazine

HRID 1272342Notes

Reaction equation

HRID 1272342 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][CH:4]=1.[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH2:23][CH2:22][N:21]([C:24]3[C:25]([CH3:38])=[C:26]([CH3:37])[C:27]4[O:31][C:30]([CH3:33])([CH3:32])[CH:29]([OH:34])[C:28]=4[C:35]=3[CH3:36])[CH2:20][CH2:19]2)=[CH:14][CH:13]=1.C(OC(C)C)(C)C.CO>>[CH3:10][O:11][C:12]1[CH:13]=[CH:14][C:15]([N:18]2[CH2:19][CH2:20][N:21]([C:24]3[C:25]([CH3:38])=[C:26]([CH3:37])[C:27]4[O:31][C:30]([CH3:33])([CH3:32])[CH:29]([O:34][CH2:2][C:3]5[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][CH:4]=5)[C:28]=4[C:35]=3[CH3:36])[CH2:22][CH2:23]2)=[CH:16][CH:17]=1

Participants

4

Reactant 3

HCID 7721p-Xylyl bromideHCID 21882575Diisopropylether methanolHCID 674202085-(4-(4-Methoxyphenyl)piperazin-1-yl)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-3-ol

Product 1

HCID 184560421-(4-Methoxyphenyl)-4-(2,2,4,6,7-pentamethyl-3-(4-methylbenzyl)oxy-2,3-dihydro-1-benzofuran-5-yl)piperazineYield 68%

Procedure

Using α-bromo-p-xylene and 5-(4-(4-methoxyphenyl)piperazin-1-yl)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-3-ol obtained in Reference Example 18, the title compound was synthesized in the same manner as in Example 74. Yield 68%. mp. 84–85° C. (diisopropyl ether-methanol). 1H-NMR (CDCl3) δ: 1.36 (3H, s), 1.59 (3H, s), 2.07 (3H, s), 2.24 (3H, s), 2.25 (3H, s), 2.33 (3H, s), 3.05–3.35 (8H, m), 3.78 (3H, s), 4.49 (2H, s), 4.66 (1H, s), 6.86 (2H, d, J=9.2 Hz), 6.97 (2H, d, J=9.2 Hz), 7.13 (2H, d, J=8.2 Hz), 7.23 (2H, d, J=8.2 Hz).

Workup

  1. customobtained in Reference Example 18

Sources & evidence

ORD record
ord-186bb96ea37c407088c6041fdbe41a55
Source dataset
uspto-grants-2007_04
Patent number
US07208495B2

Reaction notes

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