Hydrochloric Acid → 1-[3-(4-Chlorobenzoyl)propyl]-4-benzamidopiperidine

HRID 2085436Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2085436
[C:1]([NH:9][CH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:16]([O-:19])([O-])=O.[K+].[K+].[ClH:22]>CC(C)=O>[Cl:22][C:2]1[CH:7]=[CH:6][C:5]([C:16]([CH2:11][CH2:10][CH2:15][N:13]2[CH2:14][CH2:15][CH:10]([NH:9][C:1](=[O:8])[C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:11][CH2:12]2)=[O:19])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 118120N-4-Piperidylbenzamide

Produkt 1

HCID 102713911-[3-(4-Chlorobenzoyl)propyl]-4-benzamidopiperidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A mixture of 3-(4-chlorobenzol)propyl bromide (640 mg, 2.45 mmol), 4-benzamidopiperidine (500 mg, 2.45 mmol) and K2CO3 (1.01 g, 7.34 mmol) in 50 ml of acetone was heated at reflux temperature for 48 h. The cooled reaction mixture was filtered to remove the solids, concentrated in vacuo, giving a yellow solid, which was purified by chromatography (MeOH/CHCl3, 5/95). The product (320 mg 33.9%) was isolated as a white powder: 1H NMR δ 1.46 (dq, J1=1.0 Hz, J2=8.4 Hz, 2H), 1.90-2.10 (m, 4H), 2.16 (m, 2H), 2.43 (t, J=6.9 Hz, 2H), 2.80-2.90 (m, 2H), 2.97 (t, J=6.9 Hz, 2H), 3.97 (m, 1H), 5.92 (d, J=7.8 Hz, 1H, N—H), 7.40-8.00 (m, 9H). The product was converted to the HCl salt and recrystallized from MeOH/Et2O, m.p. 243-244° C.; Anal. Calcd for C22H25ClN2O2+HCl+H2O: C, 60.15; H, 6.37; N, 6.37; Found: C, 60.18; H, 6.34; N, 6.29.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux temperature for 48 h
  3. customThe cooled reaction mixture
  4. filtrationwas filtered
  5. customto remove the solids
  6. concentrationconcentrated in vacuo
  7. customgiving a yellow solid, which
  8. customwas purified by chromatography (MeOH/CHCl3, 5/95)
  9. customThe product (320 mg 33.9%) was isolated as a white powder
  10. customrecrystallized from MeOH/Et2O, m.p. 243-244° C.

Quellen und Nachweise

ORD-Eintrag
ord-add88e483c7e4c77864094a396395f6c
Quelldatensatz
uspto-grants-2004_04
Patentnummer
US06720324B2

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