1-(4-Fluorophenyl)piperazine → 1-(4-Fluorophenyl)-4-(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)piperazine

HRID 1850448Notes

Reaction equation

HRID 1850448 reaction equation
Br[C:2]1[C:3]([CH3:15])=[C:4]([CH3:14])[C:5]2[O:9][C:8]([CH3:11])([CH3:10])[CH2:7][C:6]=2[C:12]=1[CH3:13].[F:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)=[CH:19][CH:18]=1>>[F:16][C:17]1[CH:18]=[CH:19][C:20]([N:23]2[CH2:28][CH2:27][N:26]([C:2]3[C:3]([CH3:15])=[C:4]([CH3:14])[C:5]4[O:9][C:8]([CH3:11])([CH3:10])[CH2:7][C:6]=4[C:12]=3[CH3:13])[CH2:25][CH2:24]2)=[CH:21][CH:22]=1

Participants

3

Reactant 2

HCID 752601-(4-Fluorophenyl)piperazineHCID 667609285-Bromo-2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran

Product 1

HCID 594850271-(4-Fluorophenyl)-4-(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)piperazineYield 27.2%

Procedure

By using 5-bromo-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran (269 mg, 0.999 mmol) synthesized in Reference example 4 and 1-(4-fluorophenyl)piperazine (541 mg, 3.00 mmol), the reaction was carried out in the same manner as Example 21 to synthesize the title compound 100 mg (yield 27%). Melting point was 175 to 177° C. (hexane).

Sources & evidence

ORD record
ord-b2d743711e6145eca3ef4b954dd8caa0
Source dataset
uspto-grants-2015_02
Patent number
US08957069B2

Reaction notes

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