Tyramine → 6-Bromo-N-[2-(4-hydroxyphenyl)ethyl]-hexanamide

To a solution of 6-bromohexanoic acid (4.51 g, 23.1 mmol) in acetonitrile (50 mL) is added N,N'-disuccinimidyl carbonate (6.5 g, 25 mmol) and triethylamine (3.2 mL, 23 mmol). The solution is stirred at room temperature for 4 hours and tyramine (3.2 g, 23 mmol) is added and stirred continued at room temperature overnight, evaporated in vacuo, re-dissolved in ethyl acetate (100 mL) and washed with water (6×50 mL) and saturated sodium chloride solution (2×25 mL). The ethyl acetate solution is dried with sodium sulfate, filtered, and evaporated in vacuo to give a light brown gum. The crude product is purified by silica gel chromatography to give 6-bromo-N-[2-(4-hydroxyphenyl)ethyl]-hexanamide (II) as a light amber syrup.

1. stirringstirred
2. waitcontinued at room temperature overnight
3. customevaporated in vacuo
4. dissolutionre-dissolved in ethyl acetate (100 mL)
5. washwashed with water (6×50 mL) and saturated sodium chloride solution (2×25 mL)
6. dry with materialThe ethyl acetate solution is dried with sodium sulfate
7. filtrationfiltered
8. customevaporated in vacuo
9. customto give a light brown gum
10. customThe crude product is purified by silica gel chromatography

ORD record

ord-3c003b99891d49e5a0e1514eb5ffdd81

Source dataset

uspto-grants-1997_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05688966