Sodium hydride → 1-(3-{4-[1-(3-Piperidin-1-yl-propyl)-1H-pyrrol-2-yl]-phenoxy}-propyl)-piperidine

HRID 33732

Reaktionsgleichung

Reaktionsgleichung von HRID 33732
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[C:8]1[CH:23]=[CH:22][C:11]([O:12][CH2:13][CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[CH:10][CH:9]=1.Cl[CH2:25][CH2:26][CH2:27][N:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1>CN(C=O)C.O>[N:28]1([CH2:27][CH2:26][CH2:25][N:3]2[CH:7]=[CH:6][CH:5]=[C:4]2[C:8]2[CH:23]=[CH:22][C:11]([O:12][CH2:13][CH2:14][CH2:15][N:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)=[CH:10][CH:9]=2)[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 79625Piperidine, 1-(3-chloropropyl)-HCID 179626131-{3-[4-(1H-Pyrrol-2-yl)-phenoxy]-propyl}-piperidine

Produkt 1

HCID 102949771-(3-{4-[1-(3-Piperidin-1-yl-propyl)-1H-pyrrol-2-yl]-phenoxy}-propyl)-piperidineAusbeute 89,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a stirred suspension of sodium hydride (0.051 g) in DMF (3 mL) at RT was added dropwise the product of Example 18 (0.2 g) in DMF (4 mL). After 20 min, 1-(3-chloro-propyl)-piperdine (0.139 g) was added dropwise and the mixture stirred for 12 h. The mixture was diluted with water and extracted several times with diethyl ether. The combined organic layers were washed with brine, dried (sodium sulfate), filtered and concentrated under reduced pressure, giving the title compound as a dark red oil (0.257 g). 1H NMR (400 MHz, C6D6): 7.35 (d, J=8.8 Hz, 2H), 6.90 (d, J=8.8 Hz, 2H), 6.72 (t, J=2.5 Hz, 1H), 6.44 (d, J=2.5 Hz), 3.82 (m, 4H), 2.37-2.16 (m, 8H), 2.06 (br s, 4H), 1.96 (t, J=6.6 Hz, 2H), 1.87-1.81 (m, 2H), 1.59-1.22 (m, 16H).

Aufarbeitung

  1. extractionextracted several times with diethyl ether
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-cc46cb2230db48b88db4dd9f640a6651
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07429586B2

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