Hydrochloric Acid → 2-[4-(2-Hydroxyethylamino)piperidin-1-yl]-5-nitrobenzonitrile

HRID 1744535노트

반응식

HRID 1744535 반응식
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([N:12]2[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]2)=[C:8]([CH:11]=1)[C:9]#[N:10])([O-:3])=[O:2].[OH:19][CH2:20][CH2:21][NH2:22].C([BH3-])#N.[Na+].Cl>O1CCCC1.CO>[OH:19][CH2:20][CH2:21][NH:22][CH:15]1[CH2:16][CH2:17][N:12]([C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:11][C:8]=2[C:9]#[N:10])[CH2:13][CH2:14]1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 700EthanolamineHCID 5003444Sodium cyanoborohydrideHCID 222279875-Nitro-2-(4-oxopiperidin-1-yl)benzonitrile

생성물 1

HCID 222280232-[4-(2-Hydroxyethylamino)piperidin-1-yl]-5-nitrobenzonitrile

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

5-Nitro-2-(4-oxopiperidin-1-yl)benzonitrile (5.0 g), 2-hydroxyethylamine (1.5 g) and sodium cyanoborohydride (1.3 g) were added to a mixed solvent of methanol (100 ml) and tetrahydrofuran (50 ml) and the mixture was stirred at room temperature for 1 h. An aqueous hydrochloric acid solution was added to keep the reaction mixture acidic. The solvent was evaporated under reduced pressure. Aqueous sodium hydroxide solution was added to the residue and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate, after which the solvent was evaporated under reduced pressure. Diisopropyl ether was added to the residue to allow precipitation, whereby the title compound (3.6 g) was obtained, melting point: 115° C.

후처리

  1. customThe solvent was evaporated under reduced pressure
  2. additionAqueous sodium hydroxide solution was added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customafter which the solvent was evaporated under reduced pressure
  7. additionDiisopropyl ether was added to the residue
  8. customprecipitation, whereby the title compound (3.6 g)
  9. customwas obtained

출처 및 근거

ORD 기록
ord-e98d02d096044da9b509756462ea2640
출처 데이터셋
uspto-grants-2006_03
특허 번호
US07015218B1

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