Diethyl Ether → Methyl 2-[4-[2-[4-(4-pyridyl)piperazin-1-yl]acetyl]phenoxy]isobutyrate

HRID 2217

반응식

HRID 2217 반응식
Br[CH2:2][C:3]([C:5]1[CH:18]=[CH:17][C:8]([O:9][C:10]([CH3:16])([CH3:15])[C:11]([O:13][CH3:14])=[O:12])=[CH:7][CH:6]=1)=[O:4].[N:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[CH:21][CH:20]=1.C(N(CC)CC)C.C(OCC)C>C(#N)C>[N:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:26][CH2:27][N:28]([CH2:2][C:3]([C:5]3[CH:18]=[CH:17][C:8]([O:9][C:10]([CH3:16])([CH3:15])[C:11]([O:13][CH3:14])=[O:12])=[CH:7][CH:6]=3)=[O:4])[CH2:29][CH2:30]2)=[CH:21][CH:20]=1

참가 물질

6

반응물 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 705171-(4-Pyridyl)piperazineHCID 18918561Methyl 2-(4-bromoacetylphenoxy)isobutyrate

생성물 1

HCID 18918633Methyl 2-[4-[2-[4-(4-pyridyl)piperazin-1-yl]acetyl]phenoxy]isobutyrate

시약·촉매·용매 1

HCID 6342Acetonitrile용매2회

실험 절차

The product from step (i) above (2.00 g) in acetonitrile (10 ml) was added dropwise over 15 minutes to a stirred solution of 1-(4-pyridyl)piperazine (1.04 g) and triethylamine (0.89 ml) in acetonitrile (15 ml) and the mixture stirred overnight. The precipitated solid was removed by filtration and the filtrate evaporated. Purification of the residue by flash chromatography on silica, eluting with 0 to 5% v/v methanol/dichloromethane, gave a yellow gum. Trituration of this gum with diethyl ether gave methyl 2-[4-[2-[4-(4-pyridyl)piperazin-1-yl]acetyl]phenoxy]isobutyrate, 170 mg, as a white solid: m.p. 88°-90° C.; NMR (d6DMSO) δ 8.15 (2H, d), 7.96 (2H, d), 6.82 (4H, m), 3.92 (2H, s), 3.70 (3H, s), 3.33 (4H, t), 2.63 (4H, t), 1.60 (6H, s); m/e 398 (M+H)+ ; calculated for C22H27N3O4.0.25H2O: C, 65.8; H, 6.8; N, 10.5. found: C, 65.8; H, 7.1; N, 10.4%.

후처리

  1. customThe precipitated solid was removed by filtration
  2. customthe filtrate evaporated
  3. customPurification of the residue by flash chromatography on silica
  4. washeluting with 0 to 5% v/v methanol/dichloromethane
  5. customgave a yellow gum

출처 및 근거

ORD 기록
ord-f693e1231b194064866be7bc3c6466fb
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05728701

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