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Ethanol → 4-(2-{4-[2-(4-Nitrophenyl)ethyl]-3-oxopiperazin-1-yl}ethyl)benzonitrile

HRID 1466122
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HRID 1466122 반응식
O=[CH:2][CH2:3][C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][CH:5]=1.[N+:12]([C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][N:23]2[CH2:28][CH2:27][NH:26][CH2:25][C:24]2=[O:29])=[CH:17][CH:16]=1)([O-:14])=[O:13].C(O)C.C([BH3-])#N.[Na+]>C(OCC)(=O)C.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[N+:12]([C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][N:23]2[CH2:28][CH2:27][N:26]([CH2:2][CH2:3][C:4]3[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][CH:5]=3)[CH2:25][C:24]2=[O:29])=[CH:17][CH:16]=1)([O-:14])=[O:13]
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참가 물질

7

반응물 4

HCID 702EthanolHCID 5003444Sodium cyanoborohydrideHCID 125916704-(2-Oxoethyl)benzonitrileHCID 895248911-[2-(4-Nitrophenyl)ethyl]piperazin-2-one

생성물 1

HCID 895334784-(2-{4-[2-(4-Nitrophenyl)ethyl]-3-oxopiperazin-1-yl}ethyl)benzonitrile

시약·촉매·용매 2

HCID 11026
Titanium isopropoxide
촉매
HCID 8857Ethyl Acetate용매

실험 절차

The crude 4-(2-Oxoethyl)benzonitrile (100 mg, 0.69 mmol) was treated with 1-[2-(4-nitrophenyl)ethyl]piperazin-2-one (197 mg, 0.69 mmol) and titanium(IV) isopropoxide (2.0 mL). After stirring the mixture for 15 minutes, ethanol and sodium cyanoborohydride was added into the reaction. The mixture was allowed to stir for 4 hours. The reaction was diluted with ethyl acetate, washed with brine, dried over sodium sulfate, and concentrated to give the crude residue. The desired product was purified by mass-directed reverse phase HPLC (AcCN-Water with 0.1% TFA). LC-MS (IE, m/z): 378 [M+1]+.

후처리

  1. stirringto stir for 4 hours
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-1177e41e43bb4b40a8f497095486df29
출처 데이터셋
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08999990B2

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