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

HRID 2260139Notes

Reaction equation

HRID 2260139 reaction equation
[CH2:1]1[CH:6]2[C:7]3[CH:19]=[CH:18][CH:17]=[CH:16][C:8]=3[CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:5]2[CH2:4][CH2:3][N:2]1[CH2:20][CH2:21][O:22][CH2:23][C:24](O)=[O:25].[CH:27]1([NH2:33])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1.C(N(CC)CC)C.C(P(=O)(OCC)OCC)#N>O.O1CCCC1>[CH:27]1([NH:33][C:24](=[O:25])[CH2:23][O:22][CH2:21][CH2:20][N:2]2[CH2:3][CH2:4][N:5]3[C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=4[CH2:9][C:8]4[CH:16]=[CH:17][CH:18]=[CH:19][C:7]=4[CH:6]3[CH2:1]2)[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

7

Reactant 4

HCID 7965CyclohexylamineHCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 99284432-(1,2,3,4,10,14b-Hexahydrodibenzo[c,f]pyrazino[1,2-a]azepin-2-yl)ethoxyacetic acid

Product 1

HCID 18999744N-Cyclohexyl-alpha-[2-(1,2,3,4,10,14b-hexahydrodibenzo[c,f]pyrazino[1,2-a]azepin-2-yl)ethoxy]acetamideYield 91.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.358 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.

Workup

  1. additionwas added dropwise to the mixture, whilst ice-
  2. temperaturecooling
  3. extractionextracted with methylene chloride
  4. concentrationThe extract was concentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-f2b775bd064847b6a82ba30aa14e3f17
Source dataset
uspto-grants-1995_12
Patent number
US05476848

Reaction notes

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