Triethylamine → 1-[(2-Methoxy-3-piridyl)methyl]-4-(2,2-dibromovinyl)piperidine

HRID 1837689Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1837689
[CH3:1][O:2][C:3]1[C:8]([CH2:9][N:10]2[CH2:15][CH2:14][CH:13]([CH2:16]C=O)[CH2:12][CH2:11]2)=[CH:7][CH:6]=[CH:5][N:4]=1.C(N(CC)CC)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:45]([Br:49])(Br)(Br)[Br:46]>ClC(Cl)C.ClCCl>[CH3:1][O:2][C:3]1[C:8]([CH2:9][N:10]2[CH2:15][CH2:14][CH:13]([CH:16]=[C:45]([Br:49])[Br:46])[CH2:12][CH2:11]2)=[CH:7][CH:6]=[CH:5][N:4]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 226783021-[(2-Methoxy-3-pyridyl)methyl]-4-piperidineacetaldehyde

Produkt 1

HCID 226784931-[(2-Methoxy-3-piridyl)methyl]-4-(2,2-dibromovinyl)piperidineAusbeute 61,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 63651,1-DichloroethaneLösungsmittel

Versuchsvorschrift

3.0 g of 1-[(2-methoxy-3-piridyl)methyl]-4-piperidine acetaldehyde, 5.4 ml of triethylamine, 20.1 g of triphenylphosphine and 12.9 g of carbon tetrabromide were dissolved in 77 ml of dichloroethane at 0° C., and the mixture was stirred for one hour. Dichloromethane was added to the reaction solution, the mixture was washed with an aqueous saturated sodium bicarbonate, and then it was dried over anhydrous magnesium sulfate. The solvent was evaporated, and the crude product was purified by NH form silica gel column chromatography (hexane:ethyl acetate=20:1), to give 2.9 g of the title compound as a yellow oil.

Aufarbeitung

  1. washthe mixture was washed with an aqueous saturated sodium bicarbonate
  2. dry with materialit was dried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated
  4. customthe crude product was purified by NH
  5. customform silica gel column chromatography (hexane:ethyl acetate=20:1)

Quellen und Nachweise

ORD-Eintrag
ord-cf7647aa98814464817033709908698a
Quelldatensatz
uspto-grants-2004_08
Patentnummer
US06784192B2

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