Diethyl Ether → HCID 16073846, compound

HRID 1067979Notes

Reaction equation

[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([CH2:14][N:15]4[CH2:20][CH2:19][O:18][CH2:17][CH2:16]4)=[CH:11][CH:12]=3)[C:7](=[O:21])[C:6]([C:22]([O:24]CC)=O)=[CH:5]2)[CH2:3][CH2:2]1.[Cl:27][C:28]1[CH:35]=[CH:34][C:31]([CH2:32][NH2:33])=[CH:30][CH:29]=1.C(OCC)C>ClCCl>[Cl:27][C:28]1[CH:35]=[CH:34][C:31]([CH2:32][NH:33][C:22]([C:6]2[C:7](=[O:21])[C:8]3[C:13](=[CH:12][CH:11]=[C:10]([CH2:14][N:15]4[CH2:16][CH2:17][O:18][CH2:19][CH2:20]4)[CH:9]=3)[N:4]([CH:1]3[CH2:3][CH2:2]3)[CH:5]=2)=[O:24])=[CH:30][CH:29]=1

Participants

Conditions

Temperature: 165 °C

Procedure

To a flask containing ethyl 1-cyclopropyl-6-(4-morpholinylmethyl)-4-oxo-1,4-dihydro-3-quinolinecarboxylate (0.38 g) from Preparation No. 25 is added 4-chlorobenzylamine (2.0 mL). The reaction is tightly capped and heated to 165° C. overnight. The reaction is cooled to room temperature, adsorbed onto silica and chromatographed on silica eluting with 1% to 6% methanol in dichloromethane. The product-containing fractions are evaporated to give a solid which is dissolved in a minimal amount of dichloromethane. The solution is added to 1:1 diethyl ether:pentane to precipitate the title compound as a white solid. This solid is collected by filtration and dried in vacuo to afford 0.36 g of the title compound.

Workup

customfrom Preparation No
customThe reaction is tightly capped
temperatureThe reaction is cooled to room temperature
customchromatographed on silica eluting with 1% to 6% methanol in dichloromethane
customThe product-containing fractions are evaporated
customto give a solid which
custompentane to precipitate the title compound as a white solid
filtrationThis solid is collected by filtration
customdried in vacuo

Sources & evidence

ORD record: ord-a691823fc2a04a5d96e468d8da88e8b5
Source dataset: uspto-grants-2001_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06248739B1

Reaction notes

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