Benzaldehyde → 2-[3-(1-Benzylpiperidin-4-ylidene)prop-1-ynyl]-6-methylpyridine

HRID 1895959

Reaktionsgleichung

Reaktionsgleichung von HRID 1895959
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]#[C:9][CH:10]=[C:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[N:3]=1.[CH:17](=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(Cl)Cl>O>[CH2:17]([N:14]1[CH2:13][CH2:12][C:11](=[CH:10][C:9]#[C:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[N:3]=2)[CH2:16][CH2:15]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Komponenten

6

Edukt 4

HCID 240BenzaldehydeHCID 6344DichloromethaneHCID 5049666Sodium triacetoxyborohydrideHCID 875504022-Methyl-6-(3-piperidin-4-ylideneprop-1-ynyl)pyridine

Produkt 1

HCID 875507132-[3-(1-Benzylpiperidin-4-ylidene)prop-1-ynyl]-6-methylpyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of the compound of Example 3 (0.22 g, 1.04 mmol), benzaldehyde (0.13 mL, 1.25 mmol), sodium triacetoxyborohydride (0.33 g, 1.56 mmol) and 15 mL of CH2Cl2 was stirred overnight at r.t. Afterwards, it was diluted with water, the organic layer was separated, washed with brine (2×15 mL), dried (Na2SO4) and evaporated to dryness in vacuo the give a crude, which was purified by automated flash liquid chromatography (Horizon™-Biotage) eluting with a gradient Petroleum Ether-EtOAc from 85:15 to 0:100 affording the title compound, which was further purified by preparative RP LC-MS chromatography, using MS-C18 XTerra column 30×50 mm eluting with ammonium bicarbonate 20 mM pH 8 buffer-acetonitrile gradient (0.12 g).

Aufarbeitung

  1. customthe organic layer was separated
  2. washwashed with brine (2×15 mL)
  3. dry with materialdried (Na2SO4)
  4. customevaporated to dryness in vacuo the
  5. customgive a crude, which
  6. customwas purified by automated flash liquid chromatography (Horizon™-Biotage)
  7. washeluting with a gradient Petroleum Ether-EtOAc from 85:15 to 0:100 affording the title compound, which
  8. customwas further purified by preparative RP LC-MS chromatography
  9. washeluting with ammonium bicarbonate 20 mM pH 8 buffer-acetonitrile gradient (0.12 g)

Quellen und Nachweise

ORD-Eintrag
ord-901dddb84a7b4df59e8fc54be1a54a92
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08518916B2

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