Tetrahydrofuran → 1-(3-benzofuranyl)methylcarbonyl-4-(1H-indol-4-yl)piperazine

HRID 1936615노트

반응식

HRID 1936615 반응식
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([CH2:10][C:11]([OH:13])=O)=[CH:2]1.[NH:14]1[C:22]2[C:17](=[C:18]([N:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)[CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15]1.O1CCCC1>CN(C)C=O>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([CH2:10][C:11]([N:26]2[CH2:27][CH2:28][N:23]([C:18]3[CH:19]=[CH:20][CH:21]=[C:22]4[C:17]=3[CH:16]=[CH:15][NH:14]4)[CH2:24][CH2:25]2)=[O:13])=[CH:2]1

참가 물질

5

반응물 3

HCID 8028TetrahydrofuranHCID 5945904-(piperazin-1-yl)-1H-indoleHCID 27629402-(1-Benzofuran-3-yl)acetic acid

생성물 1

HCID 224622841-(3-benzofuranyl)methylcarbonyl-4-(1H-indol-4-yl)piperazine수율 25.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of 2-(3-benzofuranyl)acetic acid (0.95 g), 1-(1H-indol-4-yl)piperazine (1.3 g), and N,N-dicyclohexylcarbodiimide (1.3 g) in a mixture of dry tetrahydrofuran (50 mL) and dry dimethylformamide (10 mL) was stirred for 16 h at room temperature. Filtration and removal of solvent in vacuo gave an oil which was purified by flash chromatography (eluent: ethyl acetate/heptane/triethylamine 10:9:1) giving 1-(3-benzofuranyl)methylcarbonyl-4-(1H-indol-4-yl)piperazine (0.5 g) as an oil. The oil was dissolved in tetrahydrofuran (20 mL) and treated with a suspension of lithium aluminium hydride (0.26 g) in tetrahydrofuran (20 mL) at room temperature under a nitrogen atmosphere followed by reflux for 4 hours. The reaction mixture was cooled to 0° C. and treated subsequently with water (1 mL), 15% aq. sodium hydroxide (0.5 mL), and water (2.5 mL). After stirring for 30 min the mixture was filtered and concentrated. The remaining oil was dissolved in acetone followed by addition of oxalic acid and filtration, giving the title compound as a crystalline material (0.4 g). Mp 130-32° C. 1H NMR (DMSO-d6): 3.05-3.15 (m, 2H); 3.15-3.30 (m, 6H); 3.35 (s, 4H); 6.45 (s, 1H); 6.55 (d, 1H); 7.00 (t, 1H); 7.10 (d, 1H); 7.20-7.40 (m, 3H); 7.60 (d, 1H); 7.75 (d, 1H); 7.90 (s, 1H); 11.10 (s, 1H). MS m/z (%): 346 (MH+, 3%), 214 (31%), 199 (19%), 171 (14%).

후처리

  1. filtrationFiltration and removal of solvent in vacuo
  2. customgave an oil which
  3. customwas purified by flash chromatography (eluent: ethyl acetate/heptane/triethylamine 10:9:1)

출처 및 근거

ORD 기록
ord-01a2001f35604376b6c3b1ebd90b0877
출처 데이터셋
uspto-grants-2002_05
특허 번호
US06391882B1

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