반응 #218309

반응 방정식

1,1′-carbonyldiimidazole

4-morpholinobenzoic acid

(S)-3-amino-5-(4-methylpiperazin-1-yl)-3,4-dihydro-2H-1-benzopyran

1,1′-carbonyldiimidazole

→

title compound

수율 68.0%

(S)-N-[5-(4-Methylpiperazin-1-yl)-3,4-dihydro-2H-1-benzopyran-3-yl]-4-morpholinobenzamide

수율 68.0%

용매

N,N-dimethylformamide

N,N-dimethylformamide

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   workup.STIRRINGthe mixture was stirred for an additional 3.5 h
3. 3
   기타The solvent was removed in vacuo
4. 4
   기타the residue was purified by column chromatography on silica (eluent: chloroform/ethanol; 93:7+0.5% NH3)

실험 절차

A solution of 4-morpholinobenzoic acid (380 mg, 1.83 mmol; described in: Degutis, J.; Rasteikiene, L.; Degutiene, A. Zh. Org. Khim. 1978, 14(10), 2060-2064) and 1,1′-carbonyldiimidazole (310 mg, 1.92 mmol) in anhydrous N,N-dimethylformamide (12 mL) was stirred at 75° C. for 30 min. The mixture was allowed to cool after which a solution of (S)-3-amino-5-(4-methylpiperazin-1-yl)-3,4-dihydro-2H-1-benzopyran (430 mg, 1.74 mmol) in N,N-dimethylformamide (8 mL) was added. The reaction mixture was stirred at room temperature for 3 days. Another portion of 1,1′-carbonyldiimidazole (57 mg, 0.35 mmol) was added, and the mixture was stirred for an additional 3.5 h. The solvent was removed in vacuo, and the residue was purified by column chromatography on silica (eluent: chloroform/ethanol; 93:7+0.5% NH3) affording 513 mg (68% yield) of the title compound as a white solid: mp 210-212° C.; [α]22D −145° (c 1.0, chloroform); EIMS (70 eV) m/z (relative intensity) 436 (65, M+).

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