Hexylamine → N-(6-methylthioquinolin-5-yl)-2-hexylaminodecanamide

HRID 2379631Notes

Reaction equation

[CH3:1][S:2][C:3]1[C:4]([NH:13][C:14](=[O:25])[CH:15](Br)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[CH:6]2.[CH2:26]([NH2:32])[CH2:27][CH2:28][CH2:29][CH2:30][CH3:31].C(OCC)(=O)C>CCCCCC>[CH3:1][S:2][C:3]1[C:4]([NH:13][C:14](=[O:25])[CH:15]([NH:32][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[CH:6]2

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of N-(6-methylthioquinolin-5-yl)-2-bromodecanamide (200 mg, 0.47 mmol) and n-hexylamine (10 ml) was heated at 120° C. for 1 hour, cooled to room temperature, and chromatographed using 1:24:25/triethylamine:ethyl acetate:hexane as eluants to give the title compound as a pink oil (184 mg, 88% yield).

Workup

temperaturecooled to room temperature
customchromatographed

Sources & evidence

ORD record: ord-384cb1cac17043be8cbb7d36dedea91d
Source dataset: uspto-grants-1994_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05362878

Reaction notes

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