Acetic Acid → HCID 21963247, compound

HRID 2211930Notes

Reaction equation

HRID 2211930 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][CH:19]=3)[CH2:12][CH2:11]2)=[N:2]1.[CH:25]1[CH:30]=[C:29]([CH:31]=[O:32])[C:28]([CH:33]=O)=[CH:27][CH:26]=1.C(O)(=O)C>C(#N)C>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([N:10]2[CH2:11][CH2:12][N:13]([CH2:16][CH2:17][C:18]3[CH:19]=[CH:20][C:21]([N:24]4[CH2:33][C:28]5[C:29](=[CH:30][CH:25]=[CH:26][CH:27]=5)[C:31]4=[O:32])=[CH:22][CH:23]=3)[CH2:14][CH2:15]2)=[N:2]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4807PhthalaldehydeHCID 219631764-[2-(4-Benzo[d]isothiazol-3-yl-piperazin-1-yl)-ethyl]-phenylamine

Product 1

HCID 21963247HCID 21963247, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-[2-(4-Benzo[d]isothiazol-3-yl-piperazin-1-yl)-ethyl]-phenylamine (338.4 mg, 1.0 mmol) was reacted at reflux for 30 min with o-phthaldialdehyde (147.5 mg, 1.1 mmol) and a catalytic amount of acetic acid (57 μL, 0.1 mmol) in acetonitrile (100 mL) to give the title compound. The product obtained was purified by elution through a flash column (silica gel 40, 230–400 mesh, 100:8:1, CH2Cl:EtOH:NH4OH) to give a yellow crystalline material, yield=245 mg (53.9%). mp 175.9° C. MS (APCI): 455 [M+H]+. 1H-NMR (dmso-d6, δ): 2.59 (m, 2H) 2.66 (m, 4H) 2.77 (m, 2H) 3.43 (m, 4H) 4.98 (s, 2H) 7.30 (d, J=8.79 Hz, 2H) 7.40 (dd, J=8.67, 7.45 Hz, 1H) 7.52 (m, 2H) 7.64 (m, 2H) 7.77 (m, 3H) 8.03 (d, J=9.28 Hz, 2H).

Sources & evidence

ORD record
ord-a903e72762a04ac3aef6e98d7a80bb23
Source dataset
uspto-grants-2006_09
Patent number
US07101886B2

Reaction notes

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