Piperidine → 2-(4-Piperidinopropoxyphenyl)-7-methylimidazo[1,2-a]pyridine

HRID 1268671Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1268671
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:13]=[C:14]3[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][N:15]3[CH:21]=2)=[CH:8][CH:7]=1.[NH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1>>[N:22]1([CH2:2][CH2:3][CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([C:12]3[N:13]=[C:14]4[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][N:15]4[CH:21]=3)=[CH:8][CH:7]=2)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Komponenten

3

Edukt 2

HCID 8082PiperidineHCID 142014602-(4-Chloropropoxyphenyl)-7-methylimidazo[1,2-a]pyridine

Produkt 1

HCID 102914892-(4-Piperidinopropoxyphenyl)-7-methylimidazo[1,2-a]pyridine

Versuchsvorschrift

The product of Step C (0.2 g) and piperidine (2.0 mL) were heated at reflux temperature for 5 hours. The reaction was cooled to ambient temperature and partitioned between ethyl acetate (10 mL) and saturated sodium bicarbonate solution (10 mL). The aqueous portion was extracted with additional ethyl acetate (10 mL) and the organic portions combined. The organic portions were dried over magnesium sulfate, filtered and evaporated. The residue was purified via silica gel chromatography (dichloromethane/methanol) to give the title compound (0.21 g). This compound can also be named as 7-(methyl-2-[4-(3-piperidin-1-yl-propoxy)-phenyl]-imidazo[1,2-a]pyridine. Treatment with 2M HCl in ether afforded the dihydrochloride. 1H NMR (CD3OD) δ 8.67 (d, J=7.5 Hz, 1H), 8.41 (s, 1H), 7.84 (m, 2H), 7.71 (s, 1H), 7.36 (dd, J=6.9 Hz, J=1.4 Hz, 1H), 7.16 (m, 2H), 4.22 (t, J=5.8 Hz, 2H), 3.64 (d, J=12.5 Hz, 2H), 3.35 (m, 2H), 3.04 (m, 2H), 2.62 (s, 3H), 2.34 (m, 2H), 1.99 (m, 2H), 1.86 (m, 3H), 1.59 (m, 1H); 13C NMR (CD3OD) δ 161.0, 147.1, 141.1, 136.2, 128.5, 128.2, 120.3, 119.3, 115.8, 110.6, 109.9, 65.8, 55.0, 53.8, 24.5, 23.6, 22.1, 21.2, MS (M+H)=350.2 Analysis: Calc'd for C22H27N3O·2HCl·(2H2O)C, 57.64; H, 7.26; N, 9.17. Found: C, 57.68; H, 7.13; N, 9.16.

Aufarbeitung

  1. temperatureat reflux temperature for 5 hours
  2. custompartitioned between ethyl acetate (10 mL) and saturated sodium bicarbonate solution (10 mL)
  3. extractionThe aqueous portion was extracted with additional ethyl acetate (10 mL)
  4. dry with materialThe organic portions were dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified via silica gel chromatography (dichloromethane/methanol)

Quellen und Nachweise

ORD-Eintrag
ord-b586fb16db774cfc96b36bc626c9a7ca
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07199117B2

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