Potassium Carbonate → 4-(4-Fluorobenzyl)-1-(2-(2-oxo-1,3-dihydroindol-5-oxy)ethyl)piperidine

HRID 1955257ノート

反応式

HRID 1955257 の反応式
[O:1]=[C:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:11][CH2:12][CH2:13]OS(C3C=CC(C)=CC=3)(=O)=O)[CH:8]=2)[NH:3]1.[F:25][C:26]1[CH:38]=[CH:37][C:29]([CH2:30][CH:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)=[CH:28][CH:27]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[F:25][C:26]1[CH:27]=[CH:28][C:29]([CH2:30][CH:31]2[CH2:32][CH2:33][N:34]([CH2:13][CH2:12][O:11][C:7]3[CH:8]=[C:9]4[C:4](=[CH:5][CH:6]=3)[NH:3][C:2](=[O:1])[CH2:10]4)[CH2:35][CH2:36]2)=[CH:37][CH:38]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 36998414-(4-Fluoro-benzyl)-piperidineHCID 54323087HCID 54323087、化合物

生成物 1

HCID 232942774-(4-Fluorobenzyl)-1-(2-(2-oxo-1,3-dihydroindol-5-oxy)ethyl)piperidine収率 76%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A suspension of toluene-4-sulfonic acid 2-(2-oxo-2,3-dihydro-1H-indol-5-yloxy)-ethyl ester (0.77 g, 2.22 mmol), 4-(4-fluorobenzyl)piperidine (1.1 g, 5.63 mmol), and potassium carbonate (2.2 g, 15.92 mmol) in acetonitrile (75 ml) was refluxed overnight under argon. The reaction mixture was cooled to room temperature and the solid was filtered off and washed with THF (3×20 ml). The filtrate was evaporated, and the solid chromatographed on silica gel eluting with 35% methanol/ethyl acetate to give the title compound (0.62 g, 76%) as a solid, mp 149-150° C. Analysis calculated for C22H25FN2O2 ·0.14H2O: C, 71.21; H, 6.87; N, 7.55; F, 5.12. Found: C, 71.21; H, 6.68; N, 7.49; F, 5.26.

後処理

  1. temperaturewas refluxed overnight under argon
  2. filtrationthe solid was filtered off
  3. washwashed with THF (3×20 ml)
  4. customThe filtrate was evaporated
  5. customthe solid chromatographed on silica gel eluting with 35% methanol/ethyl acetate

出典と根拠

ORDレコード
ord-864d5909d54c406ea7497077cc0e6f41
出典データセット
uspto-grants-2000_09
特許番号
US06124323

反応ノート

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