Water → HCID 19387887, compound

HRID 1757443Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH2:7][CH:8]([C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16](=O)[CH2:15][CH2:14]2)[CH2:9][CH3:10].O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCOCC1>[NH2:7][CH:8]([C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[NH:17][CH2:16][CH2:15][CH2:14]2)[CH2:9][CH3:10]

Participants

Conditions

Temperature: 70 °C

Procedure

Example P-10:0.6 g of lithium aluminium hydride in 30 ml of absolute dioxane are placed under nitrogen in a sulfonation flask. The internal temperature is then increased to approximately 70° C. and a solution of 1.2 g of 6-(1-aminopropyl)-3,4-dihydro-quinolin-2-one in 30 mlof absolute dioxane is added dropwise over a period of 10 minutes. The batch is then stirred for 6 hours at an internal temperature of approximately 80°-85° C. and allowed to cool, and, while cooling with ice, water is added dropwise until all the excess lithium aluminium hydride has reacted. Approximately 40 ml of dioxane and sodium sulfate (approximately 10 g) are then added. After having stood for a short while, the batch is suction-filtered and the dioxane is removed under a water-jet pump vacuum. The dark-brown oil which remains can then be further purified by flash chromatography on silica gel (eluant: ethanol/ether 1:1) to yield 1.0 g of 6-(1-aminopropyl)-1,2,3,4-tetrahydro-quinoline in the form of a brown oil (1H-NMR).

Workup

temperatureto cool
customhas reacted
filtrationthe batch is suction-filtered
customthe dioxane is removed under a water-jet pump vacuum
customThe dark-brown oil which remains can then be further purified by flash chromatography on silica gel (eluant: ethanol/ether 1:1)

Sources & evidence

ORD record: ord-d73e4827251e44b29afb34ffed82cfe3
Source dataset: uspto-grants-1995_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05446040

Reaction notes

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