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

HRID 7141

Reaktionsgleichung

Reaktionsgleichung von HRID 7141
[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-ea0c4929da2f428f81be0a64ddc30905
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07084155B2

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