[C:1](Cl)(=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[NH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1.C(N(CC)CC)C.Cl>O1CCCC1O>[C:1]([NH:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)(=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]N-nonanoyl tyramine was prepared by adding dropwise about 2.74 moles of nonanoyl chloride to a cooled solution comprising about 1.0 g tyramine and about 2.03 ml of triethylamine in 35 ml of tetrahydrofuranol (THF). The reaction mixture was stirred at room temperature for 48 hours. It was then poured into about 70 ml of 10% HCl solution and the mixture extracted with ethyl acetate (3×50 ml). The ethyl acetate layer was separated, dried (MgSO4) and concentrated under reduced pressure to give a crude N-nonanoyl tyramine product. The product was purified by chromatography on a silica gel column eluted with methylene chloride/ethyl acetate (30:1).
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