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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2379439Generated: October 30, 2026

Cyclohexylamine → N-Cyclohexyl-alpha-[2-(1,2,3,4,10,14b-hexahydrodibenzo[c,f]pyrazino[1,2-a]azepin-2-yl)ethoxy]acetamide

https://huagongshe.com/reaction/2379439

Reaction equation

Participants

RoleNameHCIDCharge
ReactantCyclohexylamineHCID 7965—
ReactantTriethylamineHCID 8471—
ReactantDiethyl cyanophosphonateHCID 76257—
Reactant2-(1,2,3,4,10,14b-Hexahydrodibenzo[c,f]pyrazino[1,2-a]azepin-2-yl)ethoxyacetic acidHCID 9928443—
SolventWaterHCID 962—
SolventTetrahydrofuranHCID 8028—
ProductN-Cyclohexyl-alpha-[2-(1,2,3,4,10,14b-hexahydrodibenzo[c,f]pyrazino[1,2-a]azepin-2-yl)ethoxy]acetamideHCID 18999744914.9%

Reaction Steps

358 g of 2-(1,2,3,4,10,14b-hexahydrodibenzo[c,f]pyrazino[1,2-a]azepin-2-yl)ethoxyacetic acid (prepared as described in Example 2), 0.1 g of cyclohexylamine and 0.11 g of triethylamine were added to 10 ml of tetrahydrofuran, and 0.17 g of diethyl cyanophosphonate was added dropwise to the mixture, whilst ice-cooling. The mixture was then stirred at room temperature for 5 hours, after which it was mixed with water and then extracted with methylene chloride. The extract was concentrated by evaporation under reduced pressure, and the residue was subjected to column chromatography through silica gel, using 10 % by volume ethanol in ethyl acetate as the eluent, to afford 0. 4 g (yield 91%) of the title compound.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05362725
Source datasetuspto-grants-1994_11
ORD IDord-155f982b0d5144ca8feb3fbaab5a4d5c
Source noteuspto-grants-1994_11