Water → 1-Isopropyl-1,2,3,4-tetrahydroquinoline

HRID 378375Notes

Reaction equation

[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[CH:11](I)([CH3:13])[CH3:12].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:12][CH:11]([N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1)[CH3:13]

Participants

Conditions

Temperature: 60 °C

Procedure

13.8 g (0.1 mmol) of 1,2,3,4-tetrahydroquinoline was dissolved in 60 ml of N,N-dimethylformamide, followed by the addition of 21.1 g (0.124 mmol) of isopropyl iodide and 20.6 g (0.208 mol) of potassium carbonate. The obtained mixture was stirred under heating at 60° C. for 5 hours. Water was added to the resulting reaction mixture, followed by the extraction with ethyl acetate. The organic phase was washed with a saturated aqueous solution of common salt, dried over anhydrous magnesium sulfate, and concentrated in a vacuum. The obtained residue was purified by silica gel column chromatography (3% ethyl acetate/n-hexane) to give 13.1 g of the title compound as a colorless oil.

Workup

extractionfollowed by the extraction with ethyl acetate
washThe organic phase was washed with a saturated aqueous solution of common salt
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated in a vacuum
customThe obtained residue was purified by silica gel column chromatography (3% ethyl acetate/n-hexane)

Sources & evidence

ORD record: ord-5d0ca7c19ece4cfd9a405b31bdcf3932
Source dataset: uspto-grants-2000_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06030964

Reaction notes

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