Water → N-[5-(3-hydroxyphenyl)-2-pyrazinyl]-3-oxospiro[isobenzofuran-1(3H),4'-piperidine]-1'-carboxamide

HRID 480060Notes

Reaction equation

Cl.[NH:2]1[CH2:7][CH2:6][C:5]2([C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9](=[O:16])[O:8]2)[CH2:4][CH2:3]1.[OH:17][C:18]1[CH:19]=[C:20]([C:24]2[N:25]=[CH:26][C:27]([NH:30][C:31](=O)[O:32]C3C=CC=CC=3)=[N:28][CH:29]=2)[CH:21]=[CH:22][CH:23]=1.C(N(CC)CC)C.O>C(Cl)(Cl)Cl>[OH:17][C:18]1[CH:19]=[C:20]([C:24]2[N:25]=[CH:26][C:27]([NH:30][C:31]([N:2]3[CH2:7][CH2:6][C:5]4([C:15]5[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=5)[C:9](=[O:16])[O:8]4)[CH2:4][CH2:3]3)=[O:32])=[N:28][CH:29]=2)[CH:21]=[CH:22][CH:23]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of spiro[isobenzofuran-1(3H),4′-piperidine]-3-one hydrochloride (40 mg), phenyl N-[5-(3-hydroxyphenyl)-2-pyrazinyl]carbamate (51 mg) and triethylamine (119 μL) in chloroform (5 mL) was stirred at 80° C. for 2 hours. The reaction mixture was poured into water and extracted with chloroform (20 mL). The organic layer was washed with saturated saline solution (20 mL) and then dried over anhydrous Na2SO4. The concentration of the solvent left a residue, which was purified by column chromatography on silica gel (hexane/ethyl acetate=4/1 to 1/2) followed by recrystallization from ethyl ether-hexane to give the subject compound (24 mg) as colorless crystals (melting point 257-259° C.).

Workup

extractionextracted with chloroform (20 mL)
washThe organic layer was washed with saturated saline solution (20 mL)
dry with materialdried over anhydrous Na2SO4
waitThe concentration of the solvent left a residue, which
customwas purified by column chromatography on silica gel (hexane/ethyl acetate=4/1 to 1/2)
customfollowed by recrystallization from ethyl ether-hexane

Sources & evidence

ORD record: ord-76cccf61cc7e4ebdba24d0604d42b03c
Source dataset: uspto-grants-2003_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06649624B2

Reaction notes

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