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Ethylenediamine → HCID 68576326, 화합물

HRID 273069
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HRID 273069 반응식
[N:1]1([CH2:6][CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3([C:22]#[N:23])[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)=[CH:12][CH:11]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:24](N)[CH2:25][NH2:26]>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.CN1CCCC1=O>[CH3:8][OH:9].[NH3:1].[N:1]1([CH2:6][CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3([C:22]4[NH:26][CH2:25][CH2:24][N:23]=4)[CH2:17][CH2:18][O:19][CH2:20][CH2:21]3)=[CH:12][CH:11]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 2

HCID 3301EthylenediamineHCID 598373944-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-carbonitrile

생성물 2

HCID 21705897Ammonia methanolHCID 68576326HCID 68576326, 화합물수율 31%

시약·촉매·용매 2

HCID 8895Cupric acetate촉매
HCID 13387
N-methyl-2-pyrrolidone
용매

실험 절차

4-[4-(3-Pyrrolidin-1-yl-propoxy)-phenyl]-tetrahydro-pyran-4-carbonitrile (0.5 g, 3.1 mmol), ethylenediamine (1.5 mL, 22 mmol), copper (II) acetate (0.07 g, 0.3 mmol) and N-methylpyrrolidinone (1.5 mL) were combined and subjected to microwave (Smith Personal Synthesiser) irradiation at 220° C. for 1 hour. The reaction mixture was concentrated in vacuo to provide a brown oil. This was columned by flash chromatography on silica gel eluting with dichlromethane:methanol:ammonia (94:6:0.6 to 85:15:1.5) to provide the title compound (0.157 g, 31%) as a yellow oil. LRMS ESI+ m/z 358 [MH]+.

후처리

  1. customsubjected to microwave (Smith Personal Synthesiser) irradiation at 220° C. for 1 hour
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customto provide a brown oil

출처 및 근거

ORD 기록
ord-c0e9231fcdaa4491873d8572353c975f
출처 데이터셋
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07456164B2

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