1-Phenylpiperazine → HCID 11464749, compound

HRID 1394107Notes

Reaction equation

[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([NH:8][C:9]1[S:10][C:11]2[CH2:17][CH2:16][CH2:15][CH:14]([C:18]([OH:20])=O)[C:12]=2[N:13]=1)=[O:7].[C:21]1([N:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(Cl)Cl.O>[C:21]1([N:27]2[CH2:32][CH2:31][N:30]([C:18]([CH:14]3[C:12]4[N:13]=[C:9]([NH:8][C:6]([C:2]5[O:1][CH:5]=[CH:4][CH:3]=5)=[O:7])[S:10][C:11]=4[CH2:17][CH2:16][CH2:15]3)=[O:20])[CH2:29][CH2:28]2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 0 °C

Procedure

1,1-Carbonyldiimidazole (CDI, 0.31 g, 1.9 mmol) was added to a solution of 2-[(furan-2-carbonyl)amino]-4,5,6,7-tetrahydrobenzthiazol-4-carboxylic acid (0.5 g, 1.7 mmol) in CH2Cl2 (10 mL), and the resultant mixture was stirred for a period of 2 hours at room temperature. Following cooling of the suspension to 0° C., N-phenylpiperazine (0.28 g, 1.73 mmol), dissolved in CH2Cl2 (10 mL), was added dropwise over a period of 5 minutes. After stirring for 30 min at 0° C. and overnight at room temperature, there were added a few drops of water. Following drying over Na2SO4 and filtration, the solvent was removed and the residue was purified via column chromatography. The product furan-2-carboxylic acid(4-(4-phenylpiperazin-1-carbonyl)-4,5,6,7-tetrahydrobenzthiazol-2-yl]amide was obtained in a yield of 514 mg (corresponding to 69% of the theoretical yield).

Workup

additionwas added dropwise over a period of 5 minutes
dry with materialFollowing drying over Na2SO4 and filtration
customthe solvent was removed
customthe residue was purified via column chromatography

Sources & evidence

ORD record: ord-fd8cb77fc47f4fe4a61b0104bb8bb820
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07348347B2

Reaction notes

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