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

HRID 2210816
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HRID 2210816 반응식
[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
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참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

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 m 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.

후처리

  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

출처 및 근거

ORD 기록
ord-1fd163295a61495e93d10a0ae1eb21da
출처 데이터셋
uspto-grants-1995_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05461051

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