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Triethylamine → (R)-1-{4-[4-(3-Chloro-benzylidene)-piperidin-1-yl]-pyrimidin-2-yl}-ethyl butyrate

HRID 2227828
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2227828
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][CH:15]=1)[CH:6]=[C:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1.[CH2:16](N(CC)CC)[CH3:17].[C:23]([O:26][C@@H:27]([C:29]1[N:34]=[C:33](Cl)[CH:32]=[CH:31][N:30]=1)[CH3:28])(=[O:25])[CH3:24]>ClCCl>[C:23]([O:26][C@@H:27]([C:29]1[N:34]=[C:33]([N:10]2[CH2:11][CH2:12][C:7](=[CH:6][C:5]3[CH:13]=[CH:14][CH:15]=[C:3]([Cl:2])[CH:4]=3)[CH2:8][CH2:9]2)[CH:32]=[CH:31][N:30]=1)[CH3:28])(=[O:25])[CH2:24][CH2:16][CH3:17]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 223286604-(3-Chlorobenzylidene)-piperidine hydrochlorideHCID 54154993(R)-1-(4-chloropyrimidin-2-yl)-ethyl acetate

Produkt 1

HCID 53807001(R)-1-{4-[4-(3-Chloro-benzylidene)-piperidin-1-yl]-pyrimidin-2-yl}-ethyl butyrate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 4-(3-chlorobenzylidene)-piperidine hydrochloride (prepared according to the method of Example 176, Step B, 0.46 g, 2.0 mmol) and triethylamine (0.61 g, 6.0 mmol) in dichloromethane (10 mL) was added (R)-1-(4-chloropyrimidin-2-yl)-ethyl acetate (prepared according to the method of Preparation Five, 0.54 g, 2.2 mmol) and stirred at ambient temperature for 12 h. The mixture was washed successively with saturated aqueous sodium bicarbonate and water, and the organic layer was dried over sodium sulfate and filtered. The filtrate was concentrated to obtain a crude product which was purified by flash chromatography (95:5 dichloromethane:methanol) to give the title compound of Example 176, Step C as a viscous oil, 0.64 g (80%). 1H NMR (CDCl3, 300 MHz) δ0.95 (d, 6H), 1.51 (d, 3H), 1.68 (m, 2H) 2.35 (m, 2H), 2.47-2.64 (m, 4H), 3.67-3.75 (m, 4H), 5.68 (q, 1H), 6.36 (s, 1H), 6.40 (d, 1H), 6.98 (m, 1H), 7.12-7.28 (m, 3H), 8.18 (m, 1H); MS (CI) 400 (MH+).

Aufarbeitung

  1. customprepared
  2. customaccording to the method of Preparation Five, 0.54 g, 2.2 mmol) and
  3. washThe mixture was washed successively with saturated aqueous sodium bicarbonate and water
  4. dry with materialthe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. customto obtain a crude product which
  8. customwas purified by flash chromatography (95:5 dichloromethane:methanol)

Quellen und Nachweise

ORD-Eintrag
ord-1c76c56852f14d378ccd927999110ca8
Quelldatensatz
uspto-grants-2002_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06414149B1

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