Potassium Carbonate → 2-[4-(2-Piperidin-1-yl-ethoxy)-phenyl]-isoindole-1,3-dione

HRID 2242881Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16](=[O:17])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]2=[O:18])=[CH:4][CH:3]=1.Cl.Cl[CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[N:23]1([CH2:22][CH2:21][O:1][C:2]2[CH:3]=[CH:4][C:5]([N:8]3[C:16](=[O:17])[C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[C:9]3=[O:18])=[CH:6][CH:7]=2)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

Conditions

Temperature: 85 °C

Procedure

To a 50 mL vial which contained a solution of 2-(4-Hydroxy-phenyl)-isoindole-1,3-dione (239 mg, 1 mmol) and 1-(2-chloroethyl) piperidine hydrochloride (390 mg, 2 mmol) in DMF (15 mL) was added K2CO3 (600 mg, 4.5 mmol) at rt. The reaction mixture was heated to 85° C. and stirred at 85° C. for 72 h. After cooled to rt, the reaction mixture was poured into 50 mL ice-water mixture and then was extracted with EtOAc (3×30 mL). The combined organic layers were washed with water (3×30 mL), brine (30 mL) and dried over Na2SO4. After concentrated in vacuo, the residue was purified by a column chromatography on silica gel to yield the title product, (90 mg, 28%); LCMS; 97%, ESI+; Calcd: 350.4; Found m/z: 351.6 (M+1); 1HNMR (400 MHz, CDCl3) δ 1.40-1.68 (m, 6H), 2.52 (br, 4H), 2.80 (t, J=6.0 Hz, 2H), 4.15 (t, J=6.0 Hz, 2H), 7.02 (d, J=9.2 Hz, 2H), 7.32 (d, J=9.2 Hz, 2H), 7.77-7.79 (m, 2H), 7.84-7.96 (M, 2H).

Workup

temperatureAfter cooled to rt
extractionwas extracted with EtOAc (3×30 mL)
washThe combined organic layers were washed with water (3×30 mL), brine (30 mL)
dry with materialdried over Na2SO4
concentrationAfter concentrated in vacuo
customthe residue was purified by a column chromatography on silica gel

Sources & evidence

ORD record: ord-3f8d2f01128141489a4177daee1cce4b
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07674802B2

Reaction notes

Loading…