1-(Thiazol-2-yl)piperazine → 1-(2,2,4,6,7-Pentamethyl-2,3-dihydro-1-benzofuran-5-yl)-4-(1,3-thiazol-2-yl)piperazine

HRID 1850487Notes

Reaction equation

HRID 1850487 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].[S:16]1[CH:20]=[CH:19][N:18]=[C:17]1[N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1>>[CH3:10][C:8]1([CH3:11])[CH2:7][C:6]2[C:12]([CH3:13])=[C:2]([N:24]3[CH2:25][CH2:26][N:21]([C:17]4[S:16][CH:20]=[CH:19][N:18]=4)[CH2:22][CH2:23]3)[C:3]([CH3:15])=[C:4]([CH3:14])[C:5]=2[O:9]1

Participants

3

Reactant 2

HCID 9118061-(Thiazol-2-yl)piperazineHCID 667609285-Bromo-2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran

Product 1

HCID 594851171-(2,2,4,6,7-Pentamethyl-2,3-dihydro-1-benzofuran-5-yl)-4-(1,3-thiazol-2-yl)piperazineYield 36.5%

Procedure

By using 5-bromo-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran (404 mg, 1.50 mmol) synthesized in Reference example 4 and 1-(1,3-thiazol-2-yl)piperazine (508 mg, 3.00 mmol), the reaction was carried out in the same manner as Example 21 to synthesis the title compound 196 mg (yield 36%). Melting point was 150 to 151° C. (hexane-ethyl acetate).

Sources & evidence

ORD record
ord-c0ec5fdbf8f84449b7c6d87207590810
Source dataset
uspto-grants-2015_02
Patent number
US08957069B2

Reaction notes

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