Triethylamine → N-[2-(1-benzylpiperidin-4-yl)ethyl]-2-chloro-5,6-dimethyl-3-nitropyridin-4-amine

HRID 1060676

Reaktionsgleichung

Reaktionsgleichung von HRID 1060676
[NH2:1][CH2:2][CH2:3][CH:4]1[CH2:9][CH2:8][N:7]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:6][CH2:5]1.[Cl:17][C:18]1[C:23]([N+:24]([O-:26])=[O:25])=[C:22](Cl)[C:21]([CH3:28])=[C:20]([CH3:29])[N:19]=1.C(N(CC)CC)C>CN(C)C=O>[CH2:10]([N:7]1[CH2:6][CH2:5][CH:4]([CH2:3][CH2:2][NH:1][C:22]2[C:21]([CH3:28])=[C:20]([CH3:29])[N:19]=[C:18]([Cl:17])[C:23]=2[N+:24]([O-:26])=[O:25])[CH2:9][CH2:8]1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 18670022-(1-Benzylpiperidin-4-yl)ethan-1-amineHCID 121091232,4-Dichloro-5,6-dimethyl-3-nitropyridine

Produkt 1

HCID 21973806N-[2-(1-benzylpiperidin-4-yl)ethyl]-2-chloro-5,6-dimethyl-3-nitropyridin-4-amineAusbeute 60,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

A solution of 4-(2-aminoethyl)-1-benzylpiperidine (9.88 g, 45.2 mmol) in N,N-dimethylformamide was added dropwise to a solution of 2,4-dichloro-5,6-dimethyl-3-nitropyridine (10.00 g, 45.2 mmol) and triethylamine (12.6 mL, 90.5 mmol) in N,N-dimethylformamide (320 mL). The reaction mixture was allowed to stir at ambient temperature for about 20 hours and then it was concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water. The layers were separated and the aqueous layer was extracted with ethyl acetate. The organics were combined, washed with brine, dried over sodium sulfate and then concentrated under reduced pressure to provide an orange oil. The oil was purified by flash chromatography (400 mL silica gel eluting initially with 10% ethyl acetate in hexane, then with 15% ethyl acetate in hexane and finally with 40% ethyl acetate in hexane) to provide 11.00 g of N-[2-(1-benzylpiperidin-4-yl)ethyl]-2-chloro-5,6-dimethyl-3-nitropyridin-4-amine.

Aufarbeitung

  1. concentrationit was concentrated under reduced pressure
  2. customThe residue was partitioned between ethyl acetate and water
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customto provide an orange oil
  9. customThe oil was purified by flash chromatography (400 mL silica gel eluting initially with 10% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-f3c60fd7dc6b4ad6bd7a5ec809c6396d
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06525064B1

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