1-(4-Isopropylphenyl)piperazine → (2,4,6,7-Tetramethyl-5-{4-[4-(1-methylethyl)phenyl]piperazin-1-yl}-2,3-dihydro-1-benzofuran-2-yl)methanol

HRID 1850494Notes

Reaction equation

HRID 1850494 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].[CH:17]([C:20]1[CH:25]=[CH:24][C:23]([N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[CH:22][CH:21]=1)([CH3:19])[CH3:18]>>[CH3:10][C:8]1([CH2:11][OH:12])[CH2:7][C:6]2[C:13]([CH3:14])=[C:2]([N:29]3[CH2:30][CH2:31][N:26]([C:23]4[CH:24]=[CH:25][C:20]([CH:17]([CH3:19])[CH3:18])=[CH:21][CH:22]=4)[CH2:27][CH2:28]3)[C:3]([CH3:16])=[C:4]([CH3:15])[C:5]=2[O:9]1

Participants

3

Reactant 2

HCID 27595051-(4-Isopropylphenyl)piperazineHCID 66759014(5-Bromo-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran-2-yl)methanol

Product 1

HCID 59485020(2,4,6,7-Tetramethyl-5-{4-[4-(1-methylethyl)phenyl]piperazin-1-yl}-2,3-dihydro-1-benzofuran-2-yl)methanolYield 6.3%

Procedure

By using (5-bromo-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran-2-yl)methanol (330 mg, 1.16 mmol) synthesized in Reference example 123 and 1-(4-isopropylphenyl)piperazine (774 mg, 3.78 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 160 to 163° C. (ethyl acetate-hexane).

Sources & evidence

ORD record
ord-a771bafdad1e48e89779e3d6fcb30621
Source dataset
uspto-grants-2015_02
Patent number
US08957069B2

Reaction notes

Loading…