4-Cyanobenzaldehyde → N-(5,6,7,8-tetrahydro-8-quinolinyl)-4-cyanobenzylamine

HRID 983625

Reaktionsgleichung

Reaktionsgleichung von HRID 983625
[NH2:1][CH:2]1[C:11]2[N:10]=[CH:9][CH:8]=[CH:7][C:6]=2[CH2:5][CH2:4][CH2:3]1.[C:12]([C:14]1[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=1)#[N:13].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[N:10]1[C:11]2[CH:2]([NH:1][CH2:18][C:17]3[CH:20]=[CH:21][C:14]([C:12]#[N:13])=[CH:15][CH:16]=3)[CH2:3][CH2:4][CH2:5][C:6]=2[CH:7]=[CH:8][CH:9]=1

Komponenten

5

Edukt 3

HCID 660424-CyanobenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 113555648-Amino-5,6,7,8-tetrahydroquinoline

Produkt 1

HCID 22018532N-(5,6,7,8-tetrahydro-8-quinolinyl)-4-cyanobenzylamineAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 8-amino-5,6,7,8-tetrahydroquinoline (24.3 g, 164 mmol) in dichloromethane (600 mL), at room temperature, was added 4-cyanobenzaldehyde (21.5 g, 164 mmol) and sodium triacetoxyborohydride (45 g, 210 mmol). After 42 hours, the reaction was quenched with 1N NaOH (250 mL). The phases were separated and the organic phase was washed once with brine (200 mL), dried (Na2SO4), and concentrated. Purification of the crude material by flash chromatography on silica gel (5% CH3OH/CH2Cl2) provided 30.9 g (72%) of N-(5,6,7,8-tetrahydro-8-quinolinyl)-4-cyanobenzylamine as a pale yellow solid.

Aufarbeitung

  1. customthe reaction was quenched with 1N NaOH (250 mL)
  2. customThe phases were separated
  3. washthe organic phase was washed once with brine (200 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customPurification of the crude material by flash chromatography on silica gel (5% CH3OH/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-d22da6e769044db88481434a2f7a55ee
Quelldatensatz
uspto-grants-2005_03
Patentnummer
US06864265B2

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