Hydrochloric Acid → 4-(1-methylpiperidin-4-yl)-2H-isoquinolin-1-one

HRID 1783308노트

반응식

HRID 1783308 반응식
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:18])[NH:10][CH:9]=2)[CH2:4][CH2:3]1.C=O.[C:21](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl>C(#N)C>[CH3:21][N:2]1[CH2:7][CH2:6][CH:5]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:18])[NH:10][CH:9]=2)[CH2:4][CH2:3]1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 23084775HCID 23084775, 화합물

생성물 1

HCID 102434554-(1-methylpiperidin-4-yl)-2H-isoquinolin-1-one수율 19.2%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

4-(Piperidin-4-yl)-2H-isoquinolin-1-one hydrochloride (0.5 g) obtained in Example 31 and 35% aqueous formalin solution (0.33 g) were dissolved in acetonitrile (20 mL), and sodium triacetoxyborohydride (0.81 g) was added under ice-cooling, and the mixture was stirred at room temperature for 3 hrs. After the completion of the reaction, diluted hydrochloric acid was added to the reaction mixture. The mixture was once heated under reflux, and the solvent was evaporated. Aqueous potassium carbonate solution was added to the obtained residue, and the mixture was extracted with chloroform, and purified by silica gel column chromatography (chloroform:methanol=4:1+triethylamine 2%) to give 4-(1-methylpiperidin-4-yl)-2H-isoquinolin-1-one (88 mg) as white crystals.

후처리

  1. temperaturecooling
  2. additionwas added to the reaction mixture
  3. temperatureThe mixture was once heated
  4. temperatureunder reflux
  5. customthe solvent was evaporated
  6. additionAqueous potassium carbonate solution was added to the obtained residue
  7. extractionthe mixture was extracted with chloroform
  8. custompurified by silica gel column chromatography (chloroform:methanol=4:1+triethylamine 2%)

출처 및 근거

ORD 기록
ord-0e741d8f6fb54038b7f7b283502e6682
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07501412B2

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