Hydrogen chloride-ethyl acetate → 2-(1-cyclohexyl-3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethanamine

HRID 2383019노트

반응식

HRID 2383019 반응식
C(OC(=O)[NH:7][CH2:8][C:9]([N:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]1[CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)=[O:10])(C)(C)C.Cl.CCOC(C)=O>CCOC(C)=O>[CH:21]1([CH:12]2[C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:19][CH2:20][N:11]2[C:9](=[O:10])[CH2:8][NH2:7])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]1

참가 물질

4

반응물 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 68250253Tert-butyl[2-(1-cyclohexyl-3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethyl]carbamate

생성물 1

HCID 593965892-(1-cyclohexyl-3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethanamine수율 99.4%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
50 °C

실험 절차

Tert-butyl[2-(1-cyclohexyl-3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethyl]carbamate (1.5 g) was dissolved in EtOAc (20 mL), and 4 M HCl/EtOAc (3 mL) was added thereto under ice-cooling, followed by stirring at 50° C. for 5 hours. Then, the reaction solvent was evaporated. Saturated aqueous sodium bicarbonate was added to the reaction liquid which was then extracted with chloroform. The extract was washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated and the resulting residue was purified by silica gel column chromatography (chloroform-MeOH) to obtain 2-(1-cyclohexyl-3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethanamine (1.09 g).

후처리

  1. temperatureunder ice-cooling
  2. customThen, the reaction solvent was evaporated
  3. additionSaturated aqueous sodium bicarbonate was added to the reaction liquid which
  4. extractionwas then extracted with chloroform
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was evaporated
  8. customthe resulting residue was purified by silica gel column chromatography (chloroform-MeOH)

출처 및 근거

ORD 기록
ord-7a20500d789c4f14b5e2b2c6c8b218b9
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08263607B2

반응 노트

불러오는 중…