N,N-Dimethylethylenediamine → N-[2-(dimethylamino)ethyl]-2-(5-methYl-2-thienyl)-4-quinolinamine

HRID 1464253

Reaction equation

[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][NH2:5].C([Li])CCC.[CH3:12][C:13]1[S:17][C:16]([C:18](=[N:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:27](F)(F)F)[CH3:19])=[CH:15][CH:14]=1>CCOCC>[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][NH:5][C:27]1[C:22]2[C:21](=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:20]=[C:18]([C:16]2[S:17][C:13]([CH3:12])=[CH:14][CH:15]=2)[CH:19]=1

Participants

Conditions

Temperature: -10 °C

Procedure

A solution of N,N-dimethylethylenediamine (0.66 ml, 6.0 mmol) in ether (15 mL) was treated with a commercial solution of n-butyllithium (6.0 mmol) in hexanes at -10° C., and the resultant mixture was stirred at -10° C. for 20 minutes before treatment with a solution of ketimine 12q (0.42 g, 1.5 mmol) in ether (5 mL). The mixture was stirred at -10° C. for an additional 45 minutes, and then quenched with water (0.5 mL). The organic layer was concentrated on a rotary evaporator to give a crystalline residue. Removal of colored polymeric materials on a short silica gel column by eluting quinoline 9g with hexanes/Et3N/EtOH (7:2:1) was followed by crystallization of the purified 9g from hexanes; yield 82%, mp 103°-105° C.

Workup

customquenched with water (0.5 mL)
concentrationThe organic layer was concentrated on a rotary evaporator
customto give a crystalline residue
customRemoval of colored polymeric materials on a short silica gel column
washby eluting quinoline 9g with hexanes/Et3N/EtOH (7:2:1)
customwas followed by crystallization of the
custompurified 9g from hexanes

Sources & evidence

ORD record: ord-634a4a160f614b9b88dec3304b3db6dc
Source dataset: uspto-grants-1994_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05304554

Linked notes

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