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

HRID 1955257노트

반응식

HRID 1955257 반응식
[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

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 36998414-(4-Fluoro-benzyl)-piperidineHCID 54323087HCID 54323087, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-864d5909d54c406ea7497077cc0e6f41
출처 데이터셋
uspto-grants-2000_09
특허 번호
US06124323

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