Diisopropylethylamine → 5-{4-[2-(3-Iodophenyl)ethyl]-1-piperazinyl)2-methylquinoline

HRID 15894Notes

Reaction equation

C(N(CC)C(C)C)(C)C.[CH3:10][C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[N:21]2[CH2:26][CH2:25][N:24]([CH2:27][CH2:28][C:29]3[CH:30]=[C:31]([CH:33]=[CH:34][CH:35]=3)N)[CH2:23][CH2:22]2)[N:12]=1.CS(OCCC1C=CC=C([I:49])C=1)(=O)=O>CN(C)C=O>[I:49][C:31]1[CH:30]=[C:29]([CH2:28][CH2:27][N:24]2[CH2:23][CH2:22][N:21]([C:17]3[CH:16]=[CH:15][CH:14]=[C:13]4[C:18]=3[CH:19]=[CH:20][C:11]([CH3:10])=[N:12]4)[CH2:26][CH2:25]2)[CH:35]=[CH:34][CH:33]=1

Participants

Conditions

Temperature: 90 °C

Procedure

N,N-Diisopropylethylamine (1.7 mL; 1.5 eq) was added to a solution of 2-methyl-5-(1-piperazinyl)quinoline (D3) (1.31 g; 0.9 eq) and 2-(3-iodophenyl)ethyl methanesulfonate (2.1 g) in dimethylformamide (20 mL). The reaction mixture was heated to 90° C. for 5 hours. The dark solution was concentrated under reduced pressure, and purified by ion-exchange chromatography (SCX-2), eluting with methanol-ammonia/methanol (1M), (1:0) to (0:1). The combined basic fractions were concentrated under vacuum and purified by column chromatography (SPE cartridge, SiO2) using dichloromethane-methanol (95:5) to afford the title compound (1.5 g, 60% yield).

Workup

concentrationThe dark solution was concentrated under reduced pressure
custompurified by ion-exchange chromatography (SCX-2)
washeluting with methanol-ammonia/methanol (1M), (1:0) to (0:1)
concentrationThe combined basic fractions were concentrated under vacuum
custompurified by column chromatography (SPE cartridge, SiO2)

Sources & evidence

ORD record: ord-74b35ab596ad4432bd7a38ffa65b7cee
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07732600B2

Reaction notes

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