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Water → N-(4-benzoylphenyl)-3-oxospiro[isobenzofuran-1(3H),4'-piperidine]-1'-carboxamide

HRID 480047
Notes
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Reaction equation

HRID 480047 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.[C:17]([C:25]1[CH:30]=[CH:29][C:28]([NH:31][C:32](=O)[O:33]C2C=CC=CC=2)=[CH:27][CH:26]=1)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(N(CC)CC)C.O>C(Cl)(Cl)Cl>[C:17]([C:25]1[CH:30]=[CH:29][C:28]([NH:31][C:32]([N:2]2[CH2:7][CH2:6][C:5]3([C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[C:9](=[O:16])[O:8]3)[CH2:4][CH2:3]2)=[O:33])=[CH:27][CH:26]=1)(=[O:24])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 15548170phenyl N-(4-benzoylphenyl)carbamateHCID 223806313H-spiro[isobenzofuran-1,4'-piperidin]-3-one hydrochloride

Product 1

HCID 9845361N-(4-benzoylphenyl)-3-oxospiro[isobenzofuran-1(3H),4'-piperidine]-1'-carboxamideYield 103.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of spiro[isobenzofuran-1(3H),4′-piperidine]-3-one hydrochloride (48 mg), phenyl N-(4-benzoylphenyl)carbamate (58 mg) and triethylamine (0.14 mL) 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), then dried over anhydrous Na2SO4 and concentrated. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate=4/1 to 1/2) and recrystallized from ethyl ether-hexane to give the subject compound (81 mg) as colorless crystals (melting point 161-163° C.).

Workup

  1. extractionextracted with chloroform (20 mL)
  2. washThe organic layer was washed with saturated saline solution (20 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel (hexane/ethyl acetate=4/1 to 1/2)
  6. customrecrystallized from ethyl ether-hexane

Sources & evidence

ORD record
ord-873221ed918d4f9aa60bfda38a76c215
Source dataset
uspto-grants-2003_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06649624B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes