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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2202008Generated: October 30, 2026

Triethylamine → 3-bromo-N-(3-(3,4-dihydroisoquinolin-2(1H)-yl)-2-hydroxypropyl)benzamide

https://huagongshe.com/reaction/2202008

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriethylamineHCID 8471—
Reactant3-Bromobenzoic acidHCID 11456—
Reactant1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 15908—
Reactant1-HydroxybenzotriazoleHCID 75771—
Reactant1-amino-3-(3,4-dihydroisoquinolin-2(1H)-yl)propan-2-olHCID 16790720—
SolventWaterHCID 962—
SolventDichloromethaneHCID 6344—
Product3-bromo-N-(3-(3,4-dihydroisoquinolin-2(1H)-yl)-2-hydroxypropyl)benzamideHCID 9024095277%

Reaction Conditions

Temperature25 °C

Reaction Steps

To a solution of 3-bromobenzoic acid (200 mg, 1.0 mmol) in DCM (8 mL) was added Et3N (303 mg, 3.0 mmol), EDCI (383 mg, 2.0 mmol), HOBt (270 mg, 2.0 mmol) and 1-amino-3-(3,4-dihydroisoquinolin-2(1H)-yl)propan-2-ol (247 mg, 1.2 mmol). The mixture was stirred at 25° C. for 6 h. The mixture was treated with water and extracted with EA. The organic layer was washed with NaHCO3, brine, dried over Na2SO4 and concentrated to give the title compound which was used in next step without further purification (300 mg, Yield 77%). LCMS (m/z): 390.1 (M+1).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09365519B2
Source datasetuspto-grants-2016_06
ORD IDord-3ef0a2686ee44bca94cc780e1c4771ca
Source noteuspto-grants-2016_06